Water → 1-(Quinolin-6-yl)but-1-ene-3-one

HRID 235597

Reaction equation

HRID 235597 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:20][C:21](=[O:23])[CH3:22])C=CC=CC=1.O>CS(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH:20][C:21](=[O:23])[CH3:22])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 7656536-Quinolinecarbaldehyde

Product 1

HCID 538456471-(Quinolin-6-yl)but-1-ene-3-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of quinoline-6-carboxaldehyde (5.29 g) and 1-triphenylphosphoranylidene-2-propanone (1.5 equiv) in dimethyl sulfoxide (100 ml) was stirred at room temperature for 24 hr. The solution was poured into water (600 ml) which was subsequently extracted with ethyl acetate. The dried (MgSO4) organic fraction was evaporated under reduced pressure and the residue was purified by column chromatography over silica with dichloromethane/ethyl acetate (4:1 v/v) elution to give 1-(quinolin-6-yl)but-1-ene-3-one as a white solid. Pmr spectrum (CDCl3 ; δ in ppm : 2.41 (3H,s); 6.83 (1H,d); 7.3-9.0 (7H,m).

Workup

  1. extractionwas subsequently extracted with ethyl acetate
  2. dry with materialThe dried (MgSO4) organic fraction
  3. customwas evaporated under reduced pressure
  4. customthe residue was purified by column chromatography over silica with dichloromethane/ethyl acetate (4:1 v/v) elution

Sources & evidence

ORD record
ord-20b0ed89abf444ad9da4a1a88045af98
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Linked notes

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