1-(Triphenylphosphoranylidene)acetone → HCID 57141922, compound

HRID 2049722Notes

Reaction equation

HRID 2049722 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]=O)=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:23])[CH3:22]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]=[CH:22][C:21](=[O:23])[CH3:24])=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 11777917HCID 11777917, compound

Product 1

HCID 57141922HCID 57141922, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.3 g of 3-(p-benzyloxy-m-methoxyphenyl)propionaldehyde and 2.97 g of acetylmethylenetriphenylphosphorane in 22 ml of toluene was heated under reflux for 2 hours, toluene was then evaporated and the residue was purified by a chromatography using 30 g of silica gel and recrystallization from a mixture of ethyl ether and n-hexane (1:5) afforded 1.49 g of the desired compound melting at 59.5°-60.5° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customtoluene was then evaporated
  3. customthe residue was purified by a chromatography
  4. custom30 g of silica gel and recrystallization
  5. additionfrom a mixture of ethyl ether and n-hexane (1:5)

Sources & evidence

ORD record
ord-4022a2f90c4e4442a78472e2bff716a1
Source dataset
uspto-grants-1980_04
Patent number
US04198425

Reaction notes

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