Imidazole → (E)-2-(3-tert-Butyldimethylsilyloxy-3-cyclohexylprop-1-enyl)bicyclo[3,3,0]octan-6-one

HRID 462786Notes

Reaction equation

HRID 462786 reaction equation
[CH:1]1([CH:7]([OH:19])/[CH:8]=[CH:9]/[CH:10]2[CH2:17][CH2:16][CH:15]3[CH:11]2[CH2:12][CH2:13][C:14]3=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].N1C=CN=C1.O>CN(C)C=O>[Si:24]([O:19][CH:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)/[CH:8]=[CH:9]/[CH:10]1[CH2:17][CH2:16][CH:15]2[CH:11]1[CH2:12][CH2:13][C:14]2=[O:18])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 13241017(E)-2-(3-cyclohexyl-3-hydroxyprop-1-enyl)bicyclo[3,3,0]octan-6-one

Product 1

HCID 13241020(E)-2-(3-tert-Butyldimethylsilyloxy-3-cyclohexylprop-1-enyl)bicyclo[3,3,0]octan-6-oneYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (E)-2-(3-cyclohexyl-3-hydroxyprop-1-enyl)bicyclo[3,3,0]octan-6-one (41 mg), prepared as described in Reference Example 13, and in the form of (±)-(E)-2β-(3-cyclohexyl-3α-hydroxyprop-1-enyl)bicyclo[3,3,0]octan-6-one, tert-butyldimethylchlorosilane (35 mg), and imidazole (29.5 mg) in dimethylformamide (0.25 ml) was stirred at ambient temperature for 3 hours. Water (2.5 ml) was added and the mixture was extracted with diethyl ether. The combined ethereal extracts were washed with saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulphate, and concentrated under reduced pressure to give (E)-2-(3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl)bicyclo[3,3,0]octan-6-one (57 mg), in the form of (±)-(E)-2β-(3α-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl)bicyclo[3,3,0]octan-6-one.

Workup

  1. customprepared
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f546f5ef7d54ead9bfd5e2caaaba3a3
Source dataset
uspto-grants-1985_05
Patent number
US04517202

Reaction notes

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