tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane
• CAS No.: 140185-10-0
• Molecular Formula: C₃₁H₄₁ClO₂Si
• Molecular Weight: 509.204
• Mol file: 140185-10-0.mol

Synonyms:

Chemical Property of tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane

There total 7 articles about tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane 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: 35.5%

tert-Butoxy-((2R,6R,8aR)-6-isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy)-diphenyl-silane (140185-09-7) → tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane (140185-10-0)

Guidance literature:

With hypochloric acid; In dichloromethane;

Reference yield:

7-epi-cyperone (2303-31-3) → tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane (140185-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) K naphthalenide, hexamethyldisilazane, 2.) 2-benzenesulfonyl-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h

2: 1.1 g / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

3: 90.4 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / -78 °C

5: 76 percent / tri-n-butyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 2 h / Heating

6: 35.5 percent / aq. hypochlorous acid / CH₂Cl₂

With dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; hypochloric acid; potassium naphthalene anion radical; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

(1R,4aR,7R,8aR)-8a-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalen-2(1H)-one (21683-08-9) → tert-Butoxy-[(2R,6R,8aR)-6-(1-chloromethyl-vinyl)-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy]-diphenyl-silane (140185-10-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 96.4 percent / potassium hydroxide / methanol

2: 1.) K naphthalenide, hexamethyldisilazane, 2.) 2-benzenesulfonyl-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h

3: 1.1 g / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

4: 90.4 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / -78 °C

6: 76 percent / tri-n-butyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 2 h / Heating

7: 35.5 percent / aq. hypochlorous acid / CH₂Cl₂

With dmap; potassium hydroxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; hypochloric acid; potassium naphthalene anion radical; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; toluene;

upstream raw materials:

tert-Butoxy-((2R,6R,8aR)-6-isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy)-diphenyl-silane

7-epi-cyperone

(1R,4aR,7R,8aR)-8a-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalen-2(1H)-one

(4aR,7R)-3-Hydroxy-7-isopropenyl-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Downstream raw materials:

Acetic acid 2-[(2R,4aR,6R)-6-(tert-butoxy-diphenyl-silanyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl]-allyl ester