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917-54-4 Usage

Chemical Properties

colorless to yellowish solution
InChI:InChI=1/CH3.Li/h1H3;/rCH3Li/c1-2/h1H3

917-54-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (710873)  Methyllithiumsolution  3% in 2-Methyltetrahydrofuran/cumene 917-54-4 710873-100ML 760.50CNY Detail
Aldrich (514330)  Methyllithiumsolution  3.1 M in diethoxymethane 917-54-4 514330-1L 4,924.53CNY Detail
Aldrich (514330)  Methyllithiumsolution  3.1 M in diethoxymethane 917-54-4 514330-4X25ML 1,002.69CNY Detail
Aldrich (514330)  Methyllithiumsolution  3.1 M in diethoxymethane 917-54-4 514330-100ML 878.67CNY Detail
Alfa Aesar (42992)  Methyllithium, 1-2M in ether, packaged under Argon in resealable ChemSeal? bottles    917-54-4 0.1mole 316.0CNY Detail
Alfa Aesar (42992)  Methyllithium, 1-2M in ether, packaged under Argon in resealable ChemSeal? bottles    917-54-4 0.02mole 83.0CNY Detail
Alfa Aesar (89693)  Methyllithium, 1-2M in ether    917-54-4 0.1mole 307.0CNY Detail
TCI America (M1655)  Methyllithium (ca. 3-5% in Ethyl Ether, ca. 1-2mol/L)   917-54-4 100mL 650.00CNY Detail

917-54-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name methyllithium

1.2 Other means of identification

Product number -
Other names Methyl lithium

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:917-54-4 SDS

917-54-4Synthetic route

methyl bromide
74-83-9

methyl bromide

lithium
7439-93-2

lithium

methyllithium
917-54-4

methyllithium

Conditions
ConditionsYield
In formaldehyde diethyl acetal at 10 - 30℃; for 2.5 - 7.5h;91%
reaction at -40°C;;
4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone
65457-77-4

4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone

A

methyllithium
917-54-4

methyllithium

(1S,4S)-1-Methyl-4-(1-methyl-1-phenyl-ethoxy)-cyclopent-2-enol
99474-57-4, 99474-58-5, 114790-76-0

(1S,4S)-1-Methyl-4-(1-methyl-1-phenyl-ethoxy)-cyclopent-2-enol

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h;A 86%
B 6%
methyl iodide
74-88-4

methyl iodide

methyllithium
917-54-4

methyllithium

Conditions
ConditionsYield
With n-butyllithium In hexane; dichloromethane at -40 - 20℃; for 1h; Inert atmosphere;83%
With diethyl ether; lithium
With lithium
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
3043-52-5

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

A

methyllithium
917-54-4

methyllithium

B

pentamethylpentylbenzene
75934-66-6

pentamethylpentylbenzene

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In Cyclopentane at 55℃; for 5.5h;A n/a
B 77%
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
3043-52-5

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

tert.-butyl lithium
594-19-4

tert.-butyl lithium

A

methyllithium
917-54-4

methyllithium

B

2,3,4,5,6-pentamethylneopentylbenzene
56909-25-2

2,3,4,5,6-pentamethylneopentylbenzene

Conditions
ConditionsYield
In cyclohexane at 88℃; for 3.3h;A n/a
B 63%
methyl bromide
74-83-9

methyl bromide

methyllithium
917-54-4

methyllithium

Conditions
ConditionsYield
With lithium
methylene chloride
74-87-3

methylene chloride

methyllithium
917-54-4

methyllithium

Conditions
ConditionsYield
With bromobenzene; diethyl ether; lithium
With iodobenzene; diethyl ether; lithium
With lithium
ethyllithium
811-49-4

ethyllithium

dimethylmercury
593-74-8

dimethylmercury

methyllithium
917-54-4

methyllithium

Conditions
ConditionsYield
With Petroleum ether
ethyllithium
811-49-4

ethyllithium

dimethylmercury
593-74-8

dimethylmercury

A

methyllithium
917-54-4

methyllithium

B

diethylmercury
627-44-1

diethylmercury

ethyllithium
811-49-4

ethyllithium

methyl iodide
74-88-4

methyl iodide

methyllithium
917-54-4

methyllithium

(1S,5S,7R)-7-Bromomethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane
83781-00-4

(1S,5S,7R)-7-Bromomethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane

A

methyllithium
917-54-4

methyllithium

B

(1S,7S)-exo-brevicomin
64313-75-3

(1S,7S)-exo-brevicomin

Conditions
ConditionsYield
With copper(l) iodide 1.) ether, 10 deg C, 10 min, 2.) HMPA, RT, 24 h; Yield given. Multistep reaction. Title compound not separated from byproducts;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(2R,5R)-N-benzoylcarbonyl-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine
115378-72-8

(2R,5R)-N-benzoylcarbonyl-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine

A

methyllithium
917-54-4

methyllithium

B

(R)-1-((2R,5R)-2,5-Bis-methoxymethoxymethyl-pyrrolidin-1-yl)-2-hydroxy-2-phenyl-propan-1-one
126884-67-1

(R)-1-((2R,5R)-2,5-Bis-methoxymethoxymethyl-pyrrolidin-1-yl)-2-hydroxy-2-phenyl-propan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at -80 - 35℃; Product distribution; effect of temperature and solvent on diastereomeric excess;
C17H29Li
75961-61-4

C17H29Li

A

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
3043-52-5

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B

methyllithium
917-54-4

methyllithium

C

(β-methylbutyl)-pentamethylbenzene
75934-67-7

(β-methylbutyl)-pentamethylbenzene

D

(β-methylbutyl)-1,1,2,3,5,6-hexamethyl-2,4-cyclohexadiene
75948-86-6

(β-methylbutyl)-1,1,2,3,5,6-hexamethyl-2,4-cyclohexadiene

E

(β-methylbutyl)-1,1,2,3,5,6-hexamethyl-2,5-cyclohexadiene
75948-82-2

(β-methylbutyl)-1,1,2,3,5,6-hexamethyl-2,5-cyclohexadiene

Conditions
ConditionsYield
With 1-Methylpyrrolidine; hydrogenchloride In Cyclopentane Product distribution;A 9 % Chromat.
B n/a
C 1 % Chromat.
D 38 % Chromat.
E 52 % Chromat.
C17H29Li
75961-61-4

C17H29Li

A

methyllithium
917-54-4

methyllithium

B

(β-methylbutyl)-pentamethylbenzene
75934-67-7

(β-methylbutyl)-pentamethylbenzene

Conditions
ConditionsYield
In Cyclopentane at 20℃; Kinetics;
1,1,2,3,5,6-hexamethyl-4-pentylcyclohexadienyllithium
75961-59-0

1,1,2,3,5,6-hexamethyl-4-pentylcyclohexadienyllithium

A

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
3043-52-5

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B

methyllithium
917-54-4

methyllithium

C

pentamethylpentylbenzene
75934-66-6

pentamethylpentylbenzene

D

1,1,2,3,5,6-hexamethyl-4-pentyl-2,5-cyclohexadiene
75948-83-3

1,1,2,3,5,6-hexamethyl-4-pentyl-2,5-cyclohexadiene

E

1,1,2,3,5,6-hexamethyl-4-pentyl-2,4-cyclohexadiene
75948-79-7

1,1,2,3,5,6-hexamethyl-4-pentyl-2,4-cyclohexadiene

Conditions
ConditionsYield
With hydrogenchloride; N,N,N,N,-tetramethylethylenediamine In Cyclopentane Product distribution;A 0.7 % Chromat.
B n/a
C 2 % Chromat.
D 41.0 % Chromat.
E 56.0 % Chromat.
1,1,2,3,5,6-hexamethyl-4-pentylcyclohexadienyllithium
75961-59-0

1,1,2,3,5,6-hexamethyl-4-pentylcyclohexadienyllithium

A

methyllithium
917-54-4

methyllithium

B

pentamethylpentylbenzene
75934-66-6

pentamethylpentylbenzene

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In Cyclopentane at 20℃; Kinetics;
With 1-Methylpyrrolidine In Cyclopentane at 20℃; Kinetics;
With tetrahydrofuran In Cyclopentane at 20℃; Kinetics;
1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium
79376-82-2

1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium

A

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
3043-52-5

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B

methyllithium
917-54-4

methyllithium

C

2,3,4,5,6-pentamethylneopentylbenzene
56909-25-2

2,3,4,5,6-pentamethylneopentylbenzene

D

1,1,2,3,5,6-hexamethyl-4-neopentyl-2,4-cyclohexadiene
75948-84-4

1,1,2,3,5,6-hexamethyl-4-neopentyl-2,4-cyclohexadiene

E

1,1,2,3,5,6-hexamethyl-4-neopentyl-2,5-cyclohexadiene
75948-80-0

1,1,2,3,5,6-hexamethyl-4-neopentyl-2,5-cyclohexadiene

Conditions
ConditionsYield
With tetrahydrofuran; hydrogenchloride In Cyclopentane Product distribution;A 5 % Chromat.
B n/a
C 9 % Chromat.
D 33 % Chromat.
E 54 % Chromat.
1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium
79376-82-2

1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium

A

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene
3043-52-5

1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B

methyllithium
917-54-4

methyllithium

C

2,3,4,5,6-pentamethylneopentylbenzene
56909-25-2

2,3,4,5,6-pentamethylneopentylbenzene

D

C17H29(2)H
75948-85-5

C17H29(2)H

E

C17H29(2)H
75948-81-1

C17H29(2)H

Conditions
ConditionsYield
With 1-Methylpyrrolidine; water-d2 In Cyclopentane Product distribution;A 0.1 % Chromat.
B n/a
C 0.1 % Chromat.
D n/a
E n/a
1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium
79376-82-2

1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium

A

methyllithium
917-54-4

methyllithium

B

2,3,4,5,6-pentamethylneopentylbenzene
56909-25-2

2,3,4,5,6-pentamethylneopentylbenzene

Conditions
ConditionsYield
In Cyclopentane at 20℃; Kinetics;
In Cyclopentane at 25℃; Kinetics;
With 1-Methylpyrrolidine In Cyclopentane at 20℃; Kinetics;
With tetrahydrofuran In Cyclopentane at 20℃; Kinetics;
(2S,3aR,5aR,8aR)-3a,5,5-Trimethyl-6-oxo-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalene-2-carboxylic acid
95122-04-6

(2S,3aR,5aR,8aR)-3a,5,5-Trimethyl-6-oxo-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalene-2-carboxylic acid

A

methyllithium
917-54-4

methyllithium

6,6,8-trimethyltricyclo<6.3.0.01,5>undeca-2,9-dien-4-one
95122-06-8

6,6,8-trimethyltricyclo<6.3.0.01,5>undeca-2,9-dien-4-one

Conditions
ConditionsYield
With lead(IV) acetate; copper diacetate In pyridine 3 h, dark; ref., 1 h; Yield given. Yields of byproduct given;
(+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine
72170-87-7

(+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

A

methyllithium
917-54-4

methyllithium

B

(+)-(R)-6-methylcyclohex-2-en-1-one
62392-84-1

(+)-(R)-6-methylcyclohex-2-en-1-one

Conditions
ConditionsYield
With hydrogenchloride; PriNLi; methyl iodide 1.) THF, -20 deg C; 2.) pentane; Multistep reaction;
C15H17Si(1-)*4C4H8O*Li(1+)

C15H17Si(1-)*4C4H8O*Li(1+)

A

9,9-dimethyl-9-silafluorene
13688-68-1

9,9-dimethyl-9-silafluorene

B

methyllithium
917-54-4

methyllithium

Conditions
ConditionsYield
Heating;
ethyllithium
811-49-4

ethyllithium

dimethylmercury
593-74-8

dimethylmercury

petroleum ether

petroleum ether

A

methyllithium
917-54-4

methyllithium

B

diethylmercury
627-44-1

diethylmercury

2-methylmethoxybenzene
578-58-5

2-methylmethoxybenzene

A

methyllithium
917-54-4

methyllithium

B

lithium 2-methylphenolate
83859-26-1

lithium 2-methylphenolate

C

6-lithio-2-methyl anisole

6-lithio-2-methyl anisole

Conditions
ConditionsYield
With lithium In tetrahydrofuran at -196.15℃;
2-methoxy-1,3-dimethylbenzene
1004-66-6

2-methoxy-1,3-dimethylbenzene

A

methyllithium
917-54-4

methyllithium

B

lithium 2,6-dimethylphenolate dimer
24560-29-0

lithium 2,6-dimethylphenolate dimer

C

4-lithio-2,6-dimethyl anisole

4-lithio-2,6-dimethyl anisole

Conditions
ConditionsYield
With lithium In tetrahydrofuran at -196.15℃;
lithium
7439-93-2

lithium

methyl iodide
74-88-4

methyl iodide

methyllithium
917-54-4

methyllithium

dimethylmercury
593-74-8

dimethylmercury

lithium
7439-93-2

lithium

methyllithium
917-54-4

methyllithium

Conditions
ConditionsYield
In not given
bis(pentamethylcyclopentadienyl)ytterbium
75764-11-3

bis(pentamethylcyclopentadienyl)ytterbium

lithium iodide

lithium iodide

methyllithium
917-54-4

methyllithium

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

n-butyltrimethyltin
1527-99-7

n-butyltrimethyltin

A

methyllithium
917-54-4

methyllithium

B

di-n-butyldimethylstannane
1528-00-3

di-n-butyldimethylstannane

Conditions
ConditionsYield
In tetrahydrofuran-d8 NMR-tube; molar ratio 1:1, 1:2 and excess LiBu at -60 °C and room temp.; (1)H-NMR at -60 °C and room temp.;
methyllithium
917-54-4

methyllithium

dimethyl trans-1,2-cyclopropanedicarboxylate
826-35-7

dimethyl trans-1,2-cyclopropanedicarboxylate

trans-α,α,α',α'-tetramethylcyclopropane-1,2-diyldimethanol
3193-89-3, 7731-99-9, 91367-51-0, 123886-35-1

trans-α,α,α',α'-tetramethylcyclopropane-1,2-diyldimethanol

Conditions
ConditionsYield
In diethyl ether for 2h;100%
In diethyl ether; hexane
methyllithium
917-54-4

methyllithium

cycloheptanone
502-42-1

cycloheptanone

1-methylcycloheptanol
3761-94-2

1-methylcycloheptanol

Conditions
ConditionsYield
In diethyl ether at -78℃;100%
methyllithium
917-54-4

methyllithium

3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine
68981-86-2

3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine

3-(4,4-dimethyloxazolin-2-yl)-4-methyl-1,4-dihydropyridine
68981-79-3

3-(4,4-dimethyloxazolin-2-yl)-4-methyl-1,4-dihydropyridine

Conditions
ConditionsYield
In tetrahydrofuran 1.) -78 deg C, 1 h, 2.) 0 deg C, 1 h;100%
In diethyl ether for 1h; Ambient temperature;69.3%
cyclohexenone
930-68-7

cyclohexenone

methyllithium
917-54-4

methyllithium

1-methylcyclohex-2-en-1-ol
23758-27-2

1-methylcyclohex-2-en-1-ol

Conditions
ConditionsYield
Stage #1: cyclohexenone; methyllithium With lithium bromide In 2-methyltetrahydrofuran; diethyl ether at 0℃; for 2h;
Stage #2: With ammonium chloride In 2-methyltetrahydrofuran; diethyl ether; water at 0℃; regioselective reaction;
100%
Stage #1: methyllithium With cerium(III) chloride In tetrahydrofuran; diethyl ether for 0.5h;
Stage #2: cyclohexenone In tetrahydrofuran; diethyl ether at -78℃; for 3h;
78%
Inert atmosphere; Cooling with ice;67%
tri-O-benzyl-D-arabinolactone
14233-64-8

tri-O-benzyl-D-arabinolactone

methyllithium
917-54-4

methyllithium

1-methyl-2,3,5-tri-O-benzyl-D-arabinofuranose
138811-36-6

1-methyl-2,3,5-tri-O-benzyl-D-arabinofuranose

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78℃; for 0.0833333h;100%
In tetrahydrofuran; diethyl ether at -78℃; for 6h; Inert atmosphere;86%
In tetrahydrofuran
9-tetradecynoic acid
55182-92-8

9-tetradecynoic acid

methyllithium
917-54-4

methyllithium

10-pentadecyn-2-one
98321-46-1

10-pentadecyn-2-one

Conditions
ConditionsYield
In diethyl ether for 4h; Ambient temperature;100%
2-Methyl-2-(tert-butylperoxy)cyclohexanon
25462-04-8

2-Methyl-2-(tert-butylperoxy)cyclohexanon

methyllithium
917-54-4

methyllithium

2,7-dimethyloctane-2,7-diol
19781-07-8

2,7-dimethyloctane-2,7-diol

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
2-Methyl-2-(tert-butylperoxy)cyclohexanon
25462-04-8

2-Methyl-2-(tert-butylperoxy)cyclohexanon

methyllithium
917-54-4

methyllithium

2-tert-Butylperoxy-1,2-dimethyl-cyclohexanol
109139-10-8

2-tert-Butylperoxy-1,2-dimethyl-cyclohexanol

Conditions
ConditionsYield
In diethyl ether at -78℃; for 0.5h;100%
2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester
1149-24-2

2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester

methyllithium
917-54-4

methyllithium

3,5-bis<2-(2-hydroxypropyl)>-2,6-lutidine
117860-48-7

3,5-bis<2-(2-hydroxypropyl)>-2,6-lutidine

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
2-phenylsulfanylcyclooctanone
52190-42-8

2-phenylsulfanylcyclooctanone

methyllithium
917-54-4

methyllithium

(1R,2R)-1-Methyl-2-phenylsulfanyl-cyclooctanol
101704-33-0, 125334-90-9

(1R,2R)-1-Methyl-2-phenylsulfanyl-cyclooctanol

Conditions
ConditionsYield
100%
1-benzyl-1-cyano-5-methoxy-1,2,3,4-tetrahydronaphthalene
124921-28-4

1-benzyl-1-cyano-5-methoxy-1,2,3,4-tetrahydronaphthalene

methyllithium
917-54-4

methyllithium

1-benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalene
124921-43-3

1-benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalene

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
(10S*,11R*)-11-(tert-butylcarboxamido)-10,11-dihydro-10-hydroxy-5H-dibenzocyclohepten-5-one
115878-31-4, 125133-34-8

(10S*,11R*)-11-(tert-butylcarboxamido)-10,11-dihydro-10-hydroxy-5H-dibenzocyclohepten-5-one

methyllithium
917-54-4

methyllithium

(10S*,11S*)-11-(tert-butylcarboxamido)-10,11-dihydro-10-hydroxy-5-methyl-5H-dibenzocycloheptene
125025-42-5, 125134-16-9

(10S*,11S*)-11-(tert-butylcarboxamido)-10,11-dihydro-10-hydroxy-5-methyl-5H-dibenzocycloheptene

Conditions
ConditionsYield
In tetrahydrofuran at -5℃; for 2.2h;100%
methyllithium
917-54-4

methyllithium

(3S,6S,7aR)-6-Benzyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
112522-04-0

(3S,6S,7aR)-6-Benzyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

(3S,6S,7aR)-6-Benzyl-3-isopropyl-6,7a-dimethyl-5-methylene-hexahydro-pyrrolo[2,1-b]oxazole
116914-45-5

(3S,6S,7aR)-6-Benzyl-3-isopropyl-6,7a-dimethyl-5-methylene-hexahydro-pyrrolo[2,1-b]oxazole

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h;100%
In tetrahydrofuran at -78℃;99%
methyllithium
917-54-4

methyllithium

N-(phenylselenocarbonyl) piperidine
100033-95-2

N-(phenylselenocarbonyl) piperidine

1-(1-phenylvinyl)piperidine
14990-66-0

1-(1-phenylvinyl)piperidine

Conditions
ConditionsYield
In tetrahydrofuran 1) -78 deg C, 1h, 2) -78 to 0 deg C, 1h;100%
methyllithium
917-54-4

methyllithium

3-(1H-indol-3-yl)-acrylic acid ethyl ester
110110-37-7

3-(1H-indol-3-yl)-acrylic acid ethyl ester

(E)-β-(3-Hydroxy-3-methylbutenyl)indole
134051-29-9

(E)-β-(3-Hydroxy-3-methylbutenyl)indole

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 5h; Heating;100%
In tetrahydrofuran Heating;
methyllithium
917-54-4

methyllithium

(1R,2R)-2-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopropanecarboxylic acid ethyl ester
74857-26-4

(1R,2R)-2-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopropanecarboxylic acid ethyl ester

2-[(1R,2R)-2-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopropyl]-propan-2-ol
76833-07-3

2-[(1R,2R)-2-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopropyl]-propan-2-ol

Conditions
ConditionsYield
In diethyl ether; pentane 1.) from -5 deg C to 5 deg C, 2.) room temp., 8 h;100%
methyllithium
917-54-4

methyllithium

anti-6-methyl-cis-1,5-dicarbomethoxybicyclo<3.3.0>octane
94399-73-2

anti-6-methyl-cis-1,5-dicarbomethoxybicyclo<3.3.0>octane

2-methylene-4,4,8-trimethyl-3-oxatricyclo<3.3.3.0>decane

2-methylene-4,4,8-trimethyl-3-oxatricyclo<3.3.3.0>decane

Conditions
ConditionsYield
In tetrahydrofuran100%
methyllithium
917-54-4

methyllithium

C14H20O4
85532-84-9

C14H20O4

Conditions
ConditionsYield
100%
methyllithium
917-54-4

methyllithium

Acetic acid (1S,2R,4aS,6R,8aR)-6-bromo-2,5,5,8a-tetramethyl-1-(3-oxo-pent-4-enyl)-decahydro-naphthalen-2-yl ester
94851-59-9

Acetic acid (1S,2R,4aS,6R,8aR)-6-bromo-2,5,5,8a-tetramethyl-1-(3-oxo-pent-4-enyl)-decahydro-naphthalen-2-yl ester

Acetic acid (1S,2R,4aS,6R,8aR)-6-bromo-1-(3-hydroxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yl ester
94851-60-2, 94851-63-5

Acetic acid (1S,2R,4aS,6R,8aR)-6-bromo-1-(3-hydroxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yl ester

Conditions
ConditionsYield
In diethyl ether at 0℃; for 15h;100%
methyllithium
917-54-4

methyllithium

(2Z,6E,10E)-7-Methyl-13-(2-methyl-5-oxo-cyclopent-1-enyl)-2-triethylsilanylmethyl-trideca-2,6,10-trienoic acid isopropyl ester
109271-09-2, 109271-12-7

(2Z,6E,10E)-7-Methyl-13-(2-methyl-5-oxo-cyclopent-1-enyl)-2-triethylsilanylmethyl-trideca-2,6,10-trienoic acid isopropyl ester

(2Z,6E,10E)-13-(5-Hydroxy-2,5-dimethyl-cyclopent-1-enyl)-7-methyl-2-triethylsilanylmethyl-trideca-2,6,10-trienoic acid isopropyl ester
109271-02-5, 109281-86-9

(2Z,6E,10E)-13-(5-Hydroxy-2,5-dimethyl-cyclopent-1-enyl)-7-methyl-2-triethylsilanylmethyl-trideca-2,6,10-trienoic acid isopropyl ester

Conditions
ConditionsYield
at -78℃; 1 h. then repeat;100%
(S)-2-phenylbutanoic acid
4593-90-2, 772-15-6

(S)-2-phenylbutanoic acid

methyllithium
917-54-4

methyllithium

(S)-4-phenylpentan-2-one
32587-80-7

(S)-4-phenylpentan-2-one

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; for 2.5h;100%
In diethyl ether for 4h; Ambient temperature;97%
In diethyl ether at -78 - 20℃; Inert atmosphere;82%
In diethyl ether at -78℃; for 0.5h;54%
With copper(l) cyanide Inert atmosphere;
methyllithium
917-54-4

methyllithium

((1R,3S)-1,3-Dimethyl-2-methylene-cyclohexyl)-acetic acid
85428-13-3

((1R,3S)-1,3-Dimethyl-2-methylene-cyclohexyl)-acetic acid

1-((1R,3S)-1,3-Dimethyl-2-methylene-cyclohexyl)-propan-2-one
85428-20-2

1-((1R,3S)-1,3-Dimethyl-2-methylene-cyclohexyl)-propan-2-one

Conditions
ConditionsYield
In diethyl ether 1) ice bath 2) 5h, room temperature;100%
In diethyl ether
methyllithium
917-54-4

methyllithium

Methyl-6-endo-(Methylthio)bicyclo<2.2.1>heptane-2-exo-carboxylate
64937-42-4

Methyl-6-endo-(Methylthio)bicyclo<2.2.1>heptane-2-exo-carboxylate

2-((1S,2S,4S,6S)-6-Methylsulfanyl-bicyclo[2.2.1]hept-2-yl)-propan-2-ol
91738-66-8

2-((1S,2S,4S,6S)-6-Methylsulfanyl-bicyclo[2.2.1]hept-2-yl)-propan-2-ol

Conditions
ConditionsYield
In diethyl ether for 1h; Ambient temperature;100%
methyllithium
917-54-4

methyllithium

2,2,4-trimethyltricyclo<6.3.0.04,8>undec-6-en-9-one
82995-44-6

2,2,4-trimethyltricyclo<6.3.0.04,8>undec-6-en-9-one

(3aS,5aS,8aS)-1,4,4,5a-Tetramethyl-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalen-1-ol
86105-49-9

(3aS,5aS,8aS)-1,4,4,5a-Tetramethyl-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalen-1-ol

Conditions
ConditionsYield
In hexane 1.) -78 deg C, 6 h, 2.) room temperature, overnight;100%
methyllithium
917-54-4

methyllithium

(1aS,3aS,7R,7aS)-2-Hydroxy-3a,7-dimethyl-hexahydro-cyclopropa[c]indene-1a-carboxylic acid methyl ester
85428-17-7

(1aS,3aS,7R,7aS)-2-Hydroxy-3a,7-dimethyl-hexahydro-cyclopropa[c]indene-1a-carboxylic acid methyl ester

(1aS,3aS,7R,7aS)-1a-(1-Hydroxy-1-methyl-ethyl)-3a,7-dimethyl-octahydro-cyclopropa[c]inden-2-ol
85428-18-8

(1aS,3aS,7R,7aS)-1a-(1-Hydroxy-1-methyl-ethyl)-3a,7-dimethyl-octahydro-cyclopropa[c]inden-2-ol

Conditions
ConditionsYield
In diethyl ether100%
In diethyl ether 1) ice bath 2) 1h, room temperature;100%
methyllithium
917-54-4

methyllithium

4-allyl-4-(3-methoxyphenyl)-1-methylpiperidin-3-one
124216-74-6

4-allyl-4-(3-methoxyphenyl)-1-methylpiperidin-3-one

cis-4-allyl-4-(3-methoxyphenyl)-1,3-dimethylpiperidin-3-ol
124216-79-1

cis-4-allyl-4-(3-methoxyphenyl)-1,3-dimethylpiperidin-3-ol

Conditions
ConditionsYield
In tetrahydrofuran for 0.75h; Ambient temperature;100%
methyllithium
917-54-4

methyllithium

8a-formyl-5,5-dimethyl-3,5,6,7,8,8a-hexahydro-2(1H)-naphthalenone ethylene acetal
135040-39-0

8a-formyl-5,5-dimethyl-3,5,6,7,8,8a-hexahydro-2(1H)-naphthalenone ethylene acetal

1-(5',5'-Dimethyl-5',6',7',8'-tetrahydro-3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'a-yl)-ethanol
135040-40-3

1-(5',5'-Dimethyl-5',6',7',8'-tetrahydro-3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'a-yl)-ethanol

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; for 4.5h;100%
methyllithium
917-54-4

methyllithium

3-Methyl-1-(trimethylsilyl)buta-1,2-dien-1-yl p-tolyl sulfone
136649-78-0

3-Methyl-1-(trimethylsilyl)buta-1,2-dien-1-yl p-tolyl sulfone

2,3-Dimethyl-1-(trimethylsilyl)but-2-en-1-yl p-tolyl sulfone
136649-79-1

2,3-Dimethyl-1-(trimethylsilyl)but-2-en-1-yl p-tolyl sulfone

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78℃; for 3h;100%
Yield given;
methyllithium
917-54-4

methyllithium

(8aS)-1,8a-dihydro-8a-methyl-6(2H)-azulenone
119327-09-2

(8aS)-1,8a-dihydro-8a-methyl-6(2H)-azulenone

(6ξ,8aS)-1,2,6,8a-tetrahydro-6,8a-dimethyl-6-azulenol
119327-11-6, 119327-14-9

(6ξ,8aS)-1,2,6,8a-tetrahydro-6,8a-dimethyl-6-azulenol

Conditions
ConditionsYield
In diethyl ether at -60℃; for 2.4h;100%
methyllithium
917-54-4

methyllithium

(3α,4α,7α,8aβ)-4,7,8a-trimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-3a,7-methanoazulene-9-one
76192-89-7

(3α,4α,7α,8aβ)-4,7,8a-trimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-3a,7-methanoazulene-9-one

(3aS,4S,7R,8aR)-4,7,8a,9-Tetramethyl-octahydro-3a,7-methano-azulen-9-ol

(3aS,4S,7R,8aR)-4,7,8a,9-Tetramethyl-octahydro-3a,7-methano-azulen-9-ol

Conditions
ConditionsYield
In tetrahydrofuran for 3h; Heating;100%

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