Water → HCID 178447949, compound

HRID 1250128Notes

Reaction equation

HRID 1250128 reaction equation
[Br-].[CH2:2]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][CH2:6]1)[CH2:3][CH3:4].CC([O-])(C)C.[K+].[C:37]([C:39]1[CH:46]=[CH:45][C:42]([CH:43]=O)=[CH:41][CH:40]=1)#[N:38].O>O1CCCC1>[CH2:2]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH:11]=[CH:43][C:42]2[CH:45]=[CH:46][C:39]([C:37]#[N:38])=[CH:40][CH:41]=2)[CH2:7][CH2:6]1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 660424-CyanobenzaldehydeHCID 23665647Potassium tert-butoxideHCID 178448103HCID 178448103, compound

Product 1

HCID 178447949HCID 178447949, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a mixture of 25.0 g (0.11 mol) of trans-4-propylcyclohexylmethyltriphenylphosphonium bromide and 100 ml of tetrahydrofuran (THF) was added 12.2 g (0.10 mol) of t-BuOK while maintaining a temperature of lower than −20° C., and stirred for 1 hour. Subsequently, 70 ml of solution of 12.9 g (0.10 mol) of 4-cyanobenzaldehyde in THF was added dropwise to the solution while maintaining a temperature of lower than −20° C., and stirred at the same temperature for 2 hours to react. After finishing of the reaction, 50 ml of water was added to the reaction product and then extracted with 100 ml of toluene. The organic layer thus obtained was washed with water thrice and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: toluene) to obtain 12.1 g of a crude 4-(2-(trans-4-propylcyclohexyl)vinyl)benzonitrile.

Workup

  1. temperaturewhile maintaining a temperature of lower than −20° C.
  2. stirringstirred at the same temperature for 2 hours
  3. customto react
  4. additionwas added to the reaction product
  5. extractionextracted with 100 ml of toluene
  6. customThe organic layer thus obtained
  7. washwas washed with water thrice
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-7c66edf6096441e882a3cda6a98b29e2
Source dataset
uspto-grants-2002_01
Patent number
US06337034B1

Reaction notes

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