Water → HCID 178444330, compound

HRID 2254970Notes

Reaction equation

HRID 2254970 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH:15]=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC.COC(C)(C)C>[CH:15]([C@H:12]1[CH2:13][CH2:14][C@H:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:10][CH2:11]1)=[CH:1][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 962WaterHCID 178509803HCID 178509803, compound

Product 1

HCID 178444330HCID 178444330, compoundYield 199.9%

Reagents, catalysts & solvents 2

HCID 159628Butyltriphenylphosphonium bromideCatalystHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

A suspension of 3.6 g of butyltriphenylphosphonium bromide in 40 ml of t-butyl methyl ether was placed at room temperature while gassing with argon in a sulphonation flask equipped with a thermometer, a mechanical stirrer, a dropping funnel and a solid substance addition tube, treated with 1.01 g of potassium t-butylate and stirred at room temperature for a further 1 hour. The deep orange, heterogeneous reaction mixture was subsequently cooled to -60° C. and treated within 15 minutes with a solution of 1.28 g of trans-4-(p-cyanophenyl)cyclohexanecarboxaldehyde in 10 ml of t-butyl methyl ether. The reaction mixture was stirred for a further 60 minutes while warming slowly to -30° C., then poured into 100 ml of water and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed once with 50 ml of water, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.45 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave 1.52 g (99%) of p-[trans-4-(1-pentenyl)cyclohexyl]benzonitrile (1E-pentenyl/1Z-pentenyl ratio about 5:95) as a colourless oil; Rf-value (ethyl acetate/petroleum ether vol. 3:97) 0.19.

Workup

  1. customwas placed at room temperature
  2. customwhile gassing with argon in a sulphonation flask
  3. customequipped with a thermometer, a mechanical stirrer, a dropping funnel and a solid substance addition tube
  4. temperatureThe deep orange, heterogeneous reaction mixture was subsequently cooled to -60° C.
  5. stirringThe reaction mixture was stirred for a further 60 minutes
  6. temperaturewhile warming slowly to -30° C.
  7. extractionextracted three times with 50 ml of diethyl ether each time
  8. washThe organic phases were washed once with 50 ml of water
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-537217dc70bc436981414cfc050a215f
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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