Imidazole → (E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one

HRID 462800Notes

Reaction equation

HRID 462800 reaction equation
[OH:1][CH:2]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)/[CH:3]=[CH:4]/[CH:5]1[CH2:12][CH2:11][CH:10]2[CH:6]1[CH2:7][CH2:8][C:9]2=[O:13].[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23].N1C=CN=C1.O>CN(C)C=O>[Si:26]([O:1][CH:2]([CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)/[CH:3]=[CH:4]/[CH:5]1[CH2:12][CH2:11][CH:10]2[CH:6]1[CH2:7][CH2:8][C:9]2=[O:13])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 20397204(E)-2-(3-hydroxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one

Product 1

HCID 20397195(E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-oneYield 110.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (E)-2-(3-hydroxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one (49 mg), the less polar component prepared as described in Reference Example 45 and in the form of (±)-(E)-2β-(3β-hydroxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one, tert-butyldimethylchlorosilane (31 mg), and imidazole (29 mg) in dimethylformamide (0.116 ml) was stirred at the ambient temperature for 2 hours. The mixture was then treated with water (10 ml) and extracted with diethyl ether. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure, to give (E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one (76 mg), in the form of (±)-(E)-2β-(3β-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one.

Workup

  1. customthe less polar component prepared
  2. extractionextracted with diethyl ether
  3. washThe extract was 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-02d9e31027e8462f81f5fe6381a3b8d4
Source dataset
uspto-grants-1985_05
Patent number
US04517202

Reaction notes

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