Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl (oxetan-3-ylidene)acetate

HRID 2265905Notes

Reaction equation

HRID 2265905 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.[CH3:6][O:7][C:8]([CH:10]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:9]>ClCCl>[CH3:6][O:7][C:8](=[O:9])[CH:10]=[C:3]1[CH2:2][O:1][CH2:4]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 150242543-Oxetanone

Product 1

HCID 46839994Methyl (oxetan-3-ylidene)acetateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxetan-3-one (commercially available) (50 mg, 0.69 mmol) was solved in 1 ml dichloromethane and cooled to 0-5° C. (Methoxycarbonylmethylene) triphenylphosphorane (255 mg, 0.76 mmol) was added and the mixture stirred for 15 minutes. The mixture was directly purified with column chromatography on silica gel using heptane:ethyl acetate 100:0->0:100. The product fractions were concentrated to give 57 mg (64% yield) of a white solid.

Workup

  1. additionwas added
  2. customThe mixture was directly purified with column chromatography on silica gel
  3. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-670bcc42c07f42c8ae223b43cb82cc9a
Source dataset
uspto-grants-2010_12
Patent number
US07858630B2

Reaction notes

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