1-(Triphenylphosphoranylidene)acetone → HCID 54220051, compound

HRID 980758Notes

Reaction equation

HRID 980758 reaction equation
[CH3:1][C:2]1[C:3]([CH:18]=O)=[C:4]([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:27][C:28](=[O:30])[CH3:29])C=CC=CC=1>C1(C)C=CC=CC=1>[CH:18]([C:3]1[C:2]([CH3:1])=[C:7]([O:8][CH3:9])[C:6]([CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:27][C:28](=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 14348592HCID 14348592, compound

Product 1

HCID 54220051HCID 54220051, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 4-(3,5-dimethyl-2-formyl-4-methoxyphenyl)butyrate (9.4 g) and 1-triphenylphosphoranylidene-2-propanone (21 g equiv) were heated and stirred at reflux in toluene for 48 hr. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography over silica with dichloromethane elution to give methyl 4-[2-(but-1-en-3-one-1-yl)-3,5-dimethyl-4-methoxyphenyl]butyrate as a pale yellow oil. Pmr spectrum (CDCl3 ; δ in ppm): 1.83-2.69 (6H,m); 2.25 (3H,s); 2.28 (3H,s); 2.41 (3H,s); 3.66 (3H,s); 3.70 (3H,s); 6.26 (1H,d); 6.89 (1H,s); 7.65 (1H,d).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography over silica with dichloromethane elution

Sources & evidence

ORD record
ord-18e6a959e4f541debf402734d5cc5664
Source dataset
uspto-grants-1987_01
Patent number
US04639267

Reaction notes

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