Water → HCID 178444398, compound

HRID 1249311Notes

Reaction equation

HRID 1249311 reaction equation
[Br-].[CH2:2]([C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][CH3:6].[C:34]([C:36]1[CH:41]=[CH:40][C:39]([CH:42]2[CH2:47][CH2:46][C:45](=O)[CH2:44][CH2:43]2)=[CH:38][CH:37]=1)#[N:35].O>COC(C)(C)C.O1CCCC1>[CH2:2]([C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH:14]=[C:45]2[CH2:46][CH2:47][CH:42]([C:39]3[CH:40]=[CH:41][C:36]([C:34]#[N:35])=[CH:37][CH:38]=3)[CH2:43][CH2:44]2)[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 157899134-(4-Oxocyclohexyl)benzonitrileHCID 178444493HCID 178444493, compound

Product 1

HCID 178444398HCID 178444398, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A suspension of 10.6 g of 2-(trans-4-pentylcyclohexyl)ethyl-triphenylphosphonium bromide in 100 ml of dry t-butyl methyl ether was treated portionwise under an inert gas atmosphere at 5°-10° C. with 2.2 g of potassium t-butylate and the mixture was stirred for a further 10 minutes. Subsequently, a solution of 3.5 g of 4-(p-cyanophenyl)cyclohexanone in 50 ml of tetrahydrofuran was added dropwise over a period of 30 minutes to the orange suspension. The mixture was stirred at room temperature overnight and then treated with 50 ml of water. The aqueous phase was separated and extracted with diethyl ether. The combined organic phase was washed neutral with water, dried over sodium sulphate and concentrated. The residue was chromatographed on silica gel with hexane/ethyl acetate (vol. 95:5), thereby obtaining 3.8 g of p-[4-[2-(trans-4-pentylcyclohexyl)ethylidene]cyclohexyl]benzonitrile.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe aqueous phase was separated
  3. extractionextracted with diethyl ether
  4. washThe combined organic phase was washed neutral with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel with hexane/ethyl acetate (vol. 95:5)

Sources & evidence

ORD record
ord-44b633af025345c2aabd42d99b654529
Source dataset
uspto-grants-1986_12
Patent number
US04630896

Reaction notes

Loading…