(Triphenylphosphoranylidene)acetaldehyde → (trans)-3-[3-(6-Phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propenal

HRID 280399Notes

Reaction equation

[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]#[C:12][C@@H:13]2[O:15][C@H:14]2[CH:16]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:19]>C1C=CC=CC=1>[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]#[C:12][C@@H:13]2[O:15][C@H:14]2[CH:16]=[CH:20][CH:18]=[O:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

(trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranecarboxaldehyde (80 mg, 0.36 mmole; see Example 4) and formylmethylenetriphenylphosphorane (122 mg, 0.40 mmole) were dissolved in 10 ml of dry benzene and the mixture was heated at 70° C. for 10 minutes. The mixture was then cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in ether and filtered through a plug of silica gel. Removal of solvent afforded a brown oil which was purified by chromatography (silica gel, ether-hexane 1:1) to afford 46 mg of the title compound, melting point 91°-92.5° C.

Workup

temperatureThe mixture was then cooled to room temperature
customthe solvent was removed in vacuo
filtrationfiltered through a plug of silica gel
customRemoval of solvent
customafforded a brown oil which
customwas purified by chromatography (silica gel, ether-hexane 1:1)

Sources & evidence

ORD record: ord-f3a42aadb2ab4bab935271a7637f3c33
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04588828

Reaction notes

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