m-Phenoxybenzyl cyanide → 1-Cyclopropyl-1-(4-chlorophenyl)-4-cyano-4-(3-phenoxyphenyl)-3-butene

HRID 1588878Notes

Reaction equation

HRID 1588878 reaction equation
[CH:1]1([CH:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:5][CH:6]=O)[CH2:3][CH2:2]1.[O:15]([C:22]1[CH:23]=[C:24]([CH2:28][C:29]#[N:30])[CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O-].[Na+]>CO>[CH:1]1([CH:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:5][CH:6]=[C:28]([C:29]#[N:30])[C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:23]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 40075m-Phenoxybenzyl cyanideHCID 10942334Sodium MethoxideHCID 197548433-Cyclopropyl-3-(4-chlorophenyl)propionaldehyde

Product 1

HCID 544107201-Cyclopropyl-1-(4-chlorophenyl)-4-cyano-4-(3-phenoxyphenyl)-3-buteneYield 67.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1.5 grams (0.007 mole) of 3-cyclopropyl-3-(4-chlorophenyl)propionaldehyde and 1.5 grams (0.007 mole) of 3-phenoxyphenylacetonitrile in 50 ml of methanol was stirred, and 0.7 ml of 25% sodium methoxide in methanol was added quickly. Upon completion of addition, the reaction mixture was stirred at ambient temperature for four hours. The reaction mixture was then concentrated, and the residue was taken up in 100 ml of diethyl ether. The ether solution was washed with two 100 ml portions of water. The ether layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to centrifugally accelerated, radial thin layer chromatography. Elution was accomplished using 5% diethyl ether in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.9 grams of 1-cyclopropyl-1-(4-chlorophenyl)-4-cyano-4-(3-phenoxyphenyl)-3-butene. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred at ambient temperature for four hours
  3. concentrationThe reaction mixture was then concentrated
  4. washThe ether solution was washed with two 100 ml portions of water
  5. dry with materialThe ether layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19991ec9fc4f400a89e61996861b48cf
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

Loading…