Ethanol → HCID 178444332, compound

HRID 2231808Notes

Reaction equation

HRID 2231808 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[F:6][C:7]1[CH:8]=[C:9]([CH:15]2[CH2:20][CH2:19][CH:18]([CH:21]=O)[CH2:17][CH2:16]2)[CH:10]=[CH:11][C:12]=1[C:13]#[N:14].C(O)C>CCCCCC.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC.CCOCC>[F:6][C:7]1[CH:8]=[C:9]([C@H:15]2[CH2:20][CH2:19][C@H:18](/[CH:21]=[CH:1]/[CH2:2][CH2:3][CH3:4])[CH2:17][CH2:16]2)[CH:10]=[CH:11][C:12]=1[C:13]#[N:14]

Participants

7

Reactant 3

HCID 702EthanolHCID 137104084-(3-Fluoro-4-cyanophenyl)-cyclohexanecarbaldehydeHCID 178418339Butyllithium

Product 1

HCID 178444332HCID 178444332, compound

Reagents, catalysts & solvents 3

HCID 159628Butyltriphenylphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

7.4 ml of 1.7M n-butyllithium in hexane are added, with stirring and under an atmosphere of nitrogen, to a suspension of 5.4 g of n-butyltriphenylphosphonium bromide in 100 ml of ether. After 30 minutes the orange solution is cooled to -40° and 2.1 g of 4-(3-fluoro-4-cyanophenyl)-cyclohexanecarbaldehyde in 20 ml of ether are added. After stirring for 2 hours at -40°, 60 ml of ethanol are added dropwise. The reaction mixture is then allowed to warm up to room temperature, is stirred for one hour and worked up in the customary manner. 2-fluoro-4-[trans-4-(trans-1-pentenyl)-cyclohexyl]-benzonitrile is obtained after isomerisation in the customary manner analogously to European Published Application No. 0,122,389.

Workup

  1. temperatureAfter 30 minutes the orange solution is cooled to -40°
  2. stirringis stirred for one hour

Sources & evidence

ORD record
ord-657f35821b6c4a5ebba444a5049ee3b2
Source dataset
uspto-grants-1988_11
Patent number
US04784471

Reaction notes

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