Water → 4-Cyclopropylmethoxy-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile

HRID 657494Notes

Reaction equation

HRID 657494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:22])[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:26][CH:27]1[CH2:29][CH2:28]1.O>CS(C)=O>[CH:27]1([CH2:26][O:22][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][C:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 81503BromomethylcyclopropaneHCID 594425734-(4-Fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

Product 1

HCID 594426494-Cyclopropylmethoxy-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

500 mg of 4-(4-fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile were dissolved in 10 ml of dry dimethyl sulfoxide, treated with 190 mg of potassium hydroxide and stirred for 30 min at room temperature. Subsequently, 0.17 ml of bromomethylcyclopropane were slowly added dropwise. The reaction mixture was stirred for 24 h, treated with water and extracted with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. The crude product, a clear oil, was purified by chromatography on silica gel using HEP/EA (2:1). 510 mg of the title compound were obtained as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for 24 h
  2. extractionextracted with EA
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude product, a clear oil, was purified by chromatography on silica gel using HEP/EA (2:1)

Sources & evidence

ORD record
ord-3b8184610c2c408682f11d170eb38f11
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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