Potassium Carbonate → HCID 178447974, compound

HRID 1249305Notes

Reaction equation

HRID 1249305 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH:18]=O)[CH2:14][CH2:13]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Br-].[C:21]([C:23]1[CH:48]=[CH:47][C:26]([CH2:27][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:25][CH:24]=1)#[N:22].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH:18]=[CH:27][C:26]3[CH:47]=[CH:48][C:23]([C:21]#[N:22])=[CH:24][CH:25]=3)[CH2:14][CH2:13]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2778276(4-Cyanobenzyl)triphenylphosphonium bromideHCID 178447982HCID 178447982, compound

Product 1

HCID 178447974HCID 178447974, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5.6 g of trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexanecarboxaldehyde, 10.6 g of p-cyanobenzyl-triphenylphosphonium bromide and 200 ml of dioxan was treated with 14.5 g of powdered potassium carbonate and the mixture was heated to boiling for 72 hours. After cooling, the mixture was filtered, the filtrate was concentrated and the residue was chromatographed on silica gel with hexane/diethyl ether (vol. 4:1), thereby obtaining 6.0 g of p-[2-[trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]vinyl]benzonitrile.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customthe residue was chromatographed on silica gel with hexane/diethyl ether (vol. 4:1)

Sources & evidence

ORD record
ord-3e1e059c809f4fa0a239625e61415887
Source dataset
uspto-grants-1986_12
Patent number
US04630896

Reaction notes

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