Water → HCID 178442148, compound

HRID 370689Notes

Reaction equation

HRID 370689 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)#[CH:2].C([Li])CCC.C1(O[C:32]#[N:33])C=CC=CC=1.O>O1CCCC1.CCCCCC>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([C@H:6]2[CH2:5][CH2:4][C@H:3]([C:1]#[C:2][C:32]#[N:33])[CH2:8][CH2:7]2)=[CH:10][CH:11]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 70740Phenyl cyanateHCID 178418339ButyllithiumHCID 178455713HCID 178455713, compound

Product 1

HCID 178442148HCID 178442148, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-45 °C

Procedure

A solution of 254 mg of 1-(trans-4-ethynylcyclohexyl)-4-pentylbenzene (prepared according to Example 12) in 60 ml of absolute tetrahydrofuran was placed at -45° C. in a 100 ml sulphonation flask under argon gasification and treated within 1 minute with 1.2 ml of a 1.0N solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at -45° C. for a further 15 minutes, then cooled to -78° C. and treated with 182 μl of phenyl cyanate. The mixture was stirred at -78° C. for a further 90 minutes, then poured into 200 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed a further twice with 100 ml of water each time and once with 100 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (380 mg) on silica gel with 2% ethyl acetate/petroleum ether gave 186 mg (66.6%) of trans-4-(p-pentylphenyl)cyclohexanepropiolonitrile as colourless crystals (purity 97.3%) which were recrystallized further from hexane (purity 99.3%); m.p. (C-I) 46.9° C., cl.p. (N-I) 45.4° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturecooled to -78° C.
  3. stirringThe mixture was stirred at -78° C. for a further 90 minutes
  4. extractionextracted three times with 100 ml of diethyl ether each time
  5. washThe organic phases were washed a further twice with 100 ml of water each time
  6. dry with materialonce with 100 ml of saturated sodium chloride solution, dried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c63149c715be46eabdaa56421c8e830e
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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