Triphenylphosphine → HCID 13118263, compound

HRID 1788844Notes

Reaction equation

HRID 1788844 reaction equation
C([S:4]([CH:6]1[N:9]([CH:10]([C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=S)[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:34])[CH2:7]1)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[F:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24]2[S:4][CH:6]3[N:9]([C:8](=[O:34])[CH2:7]3)[C:10]=2[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13578056HCID 13578056, compound

Product 1

HCID 13118263HCID 13118263, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.15 g of 4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-(4-fluorophenoxy)-3-thioxo-propanate, 600 mg of triphenylphosphine, and dioxan was heated under an argon atmosphere at 100° for 15 minutes. Then, the mixture was evaporated in vacuo to dryness, and the resulting oil was chromatographed on silica gel. Elution with ethyl acetate-hexane mixtures afforded 116 mg of the title compound (12% of the theoretical yield).

Workup

  1. temperaturewas heated under an argon atmosphere at 100° for 15 minutes
  2. customThen, the mixture was evaporated in vacuo to dryness
  3. customthe resulting oil was chromatographed on silica gel
  4. washElution with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-6d1cb58153a64ec1b34fdc9b4d50e442
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

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