1-(Triphenylphosphoranylidene)acetone → HCID 54517061, compound

HRID 363989Notes

Reaction equation

HRID 363989 reaction equation
[CH:1]([C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([CH3:11])=[C:5]([CH3:12])[C:4]=1[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:28][C:29](=[O:31])[CH3:30])C=CC=CC=1>C1(C)C=CC=CC=1>[O:31]=[C:29]([CH3:30])[CH:28]=[CH:1][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([CH3:11])=[C:5]([CH3:12])[C:4]=1[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 20239926HCID 20239926, compound

Product 1

HCID 54517061HCID 54517061, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 4-(2-formyl-3,4,5,6-tetramethylphenyl)butyrate (5 g) and 1-triphenylphosphoranylidene-2-propanone (6 g) in toluene (100 ml) was boiled under reflux for 24 hours. The toluene was removed by evaporation under reduced pressure and the residue was purified by column chromatography on silica gel (eluant chloroform) to give ethyl 4-[2-(3-oxo-1-butenyl)-3,4,5,6-tetramethylphenyl]butyrate (5 g) as a pale brown oil. Proton nuclear magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.24 (3H,t); 1.6-2.0 (2H,m); 2.1-2.4 (14H,m); 2.40 (3H,s); 2.5-2.8 (2H,m); 4.11 (2H,q); 6.12 (1H,d); 7.71 (1H,d).

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe toluene was removed by evaporation under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (eluant chloroform)

Sources & evidence

ORD record
ord-490188281f824e9b92287ed9f071e829
Source dataset
uspto-grants-1986_08
Patent number
US04604128

Reaction notes

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