Water → HCID 178455715, compound

HRID 1111500Notes

Reaction equation

HRID 1111500 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[CH2:19]C[C@H](C=O)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)#[N:7].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[CH:3]([C@H:2]1[CH2:1][CH2:19][C@H:14]([C:11]2[CH:10]=[CH:9][C:8]([C:6]#[N:7])=[CH:13][CH:12]=2)[CH2:15][CH2:16]1)=[CH2:4]

Participants

7

Reactant 3

HCID 962WaterHCID 178418339ButyllithiumHCID 178509803HCID 178509803, compound

Product 1

HCID 178455715HCID 178455715, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

A suspension of 2.51 g of methyltriphenylphosphonium bromide in 80 ml of absolute tetrahydrofuran was placed at -20° C. while gassing with argon in a sulphonation flask provided with a dropping funnel and a thermometer and treated with 7.6 ml of an about 0.8 M solution of butyl lithium in hexane. After stirring at -20° C. for 30 minutes, a solution of 1.0 g of trans-4-(p-cyanophenyl)cyclohexanecarboxaldehyde in 10 ml of absolute tetrahydrofuran was added dropwise at 20° C. within 5 minutes to the yellow reaction mixture, whereby the yellow colour disappeared. The mixture was now stirred at -20° C. for a further 30 minutes and then poured into 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (2.3 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave 897 mg (91%) of p-(trans-4-vinylcyclohexyl)-benzonitrile as colourless crystals; purity 99.4%. By additional crystallization from 22 ml of methanol there was obtained p-(trans-4-vinylcyclohexyl)benzonitrile in a purity of 99.95%; m.p. (C-I) 56.4° C. cl.p. 28.5° C.

Workup

  1. customwas placed at -20° C.
  2. customwhile gassing with argon in a sulphonation flask
  3. customprovided with a dropping funnel
  4. stirringThe mixture was now stirred at -20° C. for a further 30 minutes
  5. extractionextracted three times with 100 ml of diethyl ether each time
  6. washThe organic phases were washed twice with 100 ml of water each time
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e2a796af79ac4e34b141647a95eb60b5
Source dataset
uspto-grants-1990_12
Patent number
US04980486

Reaction notes

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