3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

Base Information

Chemical Name:3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene
CAS No.:327161-99-9
Molecular Formula:C₁₇H₃₄O₂Si₂
Molecular Weight:326.627
Hs Code.:

3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

Synonyms:3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

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Chemical Property of 3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

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Technology Process of 3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

There total 1 articles about 3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

: 75-77-4
chloro-trimethyl-silane

: (S)-acetylcyclohexene

: 327161-99-9
3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

Guidance literature:: With lithium diisopropyl amide;
DOI:10.1021/ol006893h

Reference yield:

: 327161-99-9
3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

: 327162-11-8
4-hydroxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: methyllithium / tetrahydrofuran; diethyl ether / 1.08 h / -78 - 0 °C

1.2: hexamethylphosphorotriamide / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.1: 4.57 g / sodium methoxide / methanol / 5.5 h / Heating

3.1: 94 percent / hydrogen fluoride / H₂O; acetonitrile / 2 h / 20 °C

4.1: 90 percent / 2 h / 20 °C

5.1: 93 percent / azobisisobutyronitrile; n-tributyltinhydride / benzene / 1 h / 60 °C

6.1: 90 percent / L-selectride; sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 11.5 h / 20 °C

7.1: 78 percent / potassium tert-butoxide / dimethylsulfoxide; 2-methyl-propan-2-ol / 23 h / 20 °C

8.1: potassium tert-butoxide / tetrahydrofuran / 0.83 h / -35 °C

9.1: 258.1 mg / tetrahydrofuran / 0.17 h

10.1: 1-methylnaphthalene / 3 h / 190 °C

11.1: 22 mg / lithium aluminium hydride / diethyl ether / 0.25 h / 0 °C

12.1: 17 mg / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

13.1: titanium(IV) chloride / CH₂Cl₂ / -78 °C

13.2: 20 mg / Jones reagent / acetone / 0 °C

14.1: 93 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / benzene / 2.5 h / 60 °C

15.1: 82 percent / acetic acid; piperidine / ethanol / 17 h / 55 °C

With piperidine; sodium hydroxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; hydrogen fluoride; potassium tert-butylate; methyllithium; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; titanium tetrachloride; L-Selectride; acetic acid; 1-Methylnaphthalene; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; benzene; 13.2: Jones oxidation;
DOI:10.1021/jo0163602

Reference yield:

: 327161-99-9
3-(tert-butyl-dimethyl-silanyloxy)-1-(1-trimethylsilanyloxy-vinyl)-cyclohexene

: 327162-12-9
4-methoxy-6-[(1R,2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-1-naphthyl]-3-phenylthiomethyl-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 16 steps

1.1: methyllithium / tetrahydrofuran; diethyl ether / 1.08 h / -78 - 0 °C

1.2: hexamethylphosphorotriamide / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.1: 4.57 g / sodium methoxide / methanol / 5.5 h / Heating

3.1: 94 percent / hydrogen fluoride / H₂O; acetonitrile / 2 h / 20 °C

4.1: 90 percent / 2 h / 20 °C

5.1: 93 percent / azobisisobutyronitrile; n-tributyltinhydride / benzene / 1 h / 60 °C

6.1: 90 percent / L-selectride; sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 11.5 h / 20 °C

7.1: 78 percent / potassium tert-butoxide / dimethylsulfoxide; 2-methyl-propan-2-ol / 23 h / 20 °C

8.1: potassium tert-butoxide / tetrahydrofuran / 0.83 h / -35 °C

9.1: 258.1 mg / tetrahydrofuran / 0.17 h

10.1: 1-methylnaphthalene / 3 h / 190 °C

11.1: 22 mg / lithium aluminium hydride / diethyl ether / 0.25 h / 0 °C

12.1: 17 mg / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

13.1: titanium(IV) chloride / CH₂Cl₂ / -78 °C

13.2: 20 mg / Jones reagent / acetone / 0 °C

14.1: 93 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / benzene / 2.5 h / 60 °C

15.1: 82 percent / acetic acid; piperidine / ethanol / 17 h / 55 °C

16.1: 77 percent / potassium carbonate / acetone / 0.5 h / 20 °C

With piperidine; sodium hydroxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; hydrogen fluoride; potassium tert-butylate; methyllithium; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; titanium tetrachloride; L-Selectride; potassium carbonate; acetic acid; 1-Methylnaphthalene; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile; tert-butyl alcohol; benzene; 13.2: Jones oxidation;
DOI:10.1021/jo0163602