Name: 3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE
SKU: 182699-77-0

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Basic Information

Molecular Structure:
CAS No.:	182699-77-0
Name:	3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE

Formula:	C10H14 O2
Molecular Weight:	166.22
Synonyms:	2(3H)-Benzofuranone,3a,4,5,7a-tetrahydro-3,6-dimethyl-, [3S-(3a,3aa,7aa)]-; (-)-(3S,3aS,7aR)-Winelactone; (-)-Wine lactone; Wine lactone
Density:	1.042 g/cm³
Boiling Point:	286.3 ºC at 760 mmHg
Flash Point:	115.5 ºC
PSA:	26.30000
LogP:	1.90420

Synthetic route

: 477717-60-5
(3aS,7aS)-6-methyl-3-methylene-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one

A: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

B: 182699-79-2
(+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
With [NH2Me2][{RuCl((S)-segphos)}2(μ-Cl)3]; hydrogen In 1,4-dioxane at 40℃; under 15001.5 Torr; for 6h; Inert atmosphere; Autoclave; diastereoselective reaction;	A n/a B 99%
With [NH2Me2][{RuCl((R)-H8-binap)}2(μ-Cl)3]; hydrogen In 1,4-dioxane at 30℃; under 15001.5 Torr; for 16h; Inert atmosphere; Autoclave; diastereoselective reaction;	A 69% B n/a
With sodium tetrahydroborate In ethanol at 20℃; for 1.5h; Product distribution; Further Variations:; Reagents;	A 5 % Chromat. B 92 % Chromat.
With magnesium In methanol at 20℃; for 3h;

: 263163-03-7
(+)-(3aS,7aR)-2,3,3a,4,5,7a-hexahydro-6-methylbenzofuran-2(3H)-one

: 74-88-4
methyl iodide

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
Stage #1: (+)-(3aS,7aR)-2,3,3a,4,5,7a-hexahydro-6-methylbenzofuran-2(3H)-one With n-butyllithium; diisopropylamine In tetrahydrofuran at -20 - 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide With 1,3-dimethyl-2-imidazolidinone In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere;	90%
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Alkylation;	79%

: 416864-79-4
(3S,3aS,6R,7R,7aR)-(3a,4,5,6,7,7a)-hexahydro-3,6-dimethylbenzofuran-2(3H)-one

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 5h;	76%

: 287720-48-3
(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanoic acid

A: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

B: 182699-79-2
(+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; dipyridinium dichromate; Celite In N,N-dimethyl-formamide at 30℃; for 12h;
With tert.-butylhydroperoxide; dipyridinium dichromate; Celite In benzene at 30℃; for 12h;

: 182699-81-6
(3S,3aS,7aS)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h; Yield given. Multistep reaction;

: 182699-83-8
(3R,3aS,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h; Yield given. Multistep reaction;

: 416864-77-2
2-((1R,4R)-4-Methyl-cyclohex-2-enyl)-propionic acid

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: FeCl3; NaI / acetonitrile / 2.5 h / Heating 2: 76 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme

: 160224-76-0
(-)-(3aS,7R,7aR)-hexahydro-7-iodo-benzo[b]furan-2-one

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 2: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 3: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 4: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 5: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

: 263163-00-4
methyl (+)-(S)-(cyclohex-2-enyl)acetate

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Yield

Multi-step reaction with 7 steps
1: 95 percent / NaOH / 1 h / 120 °C
2: 66 percent / KI; I2; NaHCO3 / H2O / 5 h / 20 °C
3: 82 percent / DBU / tetrahydrofuran / 3 h / Heating
4: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C
5: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C
6: 92 percent / DBU / tetrahydrofuran / 2 h / Heating
7: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C
View Scheme

: 34939-28-1, 78601-28-2, 138258-79-4, 78601-26-0
dimethyl 2-(cyclohex-2-en-1-yl)propanedioate

: 182699-77-0
(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Conditions

Yield

Multi-step reaction with 8 steps
1: 74 percent / NaCl / H2O; dimethylsulfoxide / 24 h / 160 °C
2: 95 percent / NaOH / 1 h / 120 °C
3: 66 percent / KI; I2; NaHCO3 / H2O / 5 h / 20 °C
4: 82 percent / DBU / tetrahydrofuran / 3 h / Heating
5: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C
6: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C
7: 92 percent / DBU / tetrahydrofuran / 2 h / Heating
8: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C
View Scheme

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- China (Mainland)(23)
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