Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 2-(oxetan-3-ylidene)acetate

HRID 1850308Notes

Reaction equation

HRID 1850308 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])C=CC=CC=1>C(Cl)Cl>[CH2:17]([O:16][C:14](=[O:15])[CH:13]=[C:3]1[CH2:2][O:1][CH2:4]1)[CH3:18]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 150242543-Oxetanone

Product 1

HCID 53308471Ethyl 2-(oxetan-3-ylidene)acetateYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of oxetan-3-one (118) (5 g, 69.4 mmol) in CH2Cl2 (50 mL) at 0° C. was added ethyl 2-triphenylphosphoranylideneacetate (119) (26.6 g, 76.3 mmol). The solution was allowed to warm to RT and stirred for 15 min. The reaction mixture was then filtered through a pad of silica (washing with 30 percent EtOAc:Petrol ether), and the solvent removed under reduced pressure to give ethyl 2-(oxetan-3-ylidene)acetate (120) as a colourless viscous oil (8.15 g, 57.4 mmol, yield: 79%). ESI-MS (M+1): 142 calc. for C7H10O3 142.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of silica (washing with 30 percent EtOAc:Petrol ether)
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0785b78fd18b4b6796af45d051ab5b42
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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