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

HRID 384076Notes

Reaction equation

HRID 384076 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>[O:1]1[CH2:2][C:3](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4]1

Participants

4

Reactant 2

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

Product 1

HCID 53308471Ethyl 2-(oxetan-3-ylidene)acetateYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of oxetan-3-one (500 mg, 6.938 mmol) in DCM (15.00 mL) at 0° C. was added ethyl 2-triphenylphosphoranylideneacetate (2.659 g, 7.632 mmol). The solution was allowed to warm to room temperature and stirred for 15 minutes. The reaction mixture was then filtered through a pad of silica (washing with 30% EtOAc:Petrol ether), and the solvent removed under reduced pressure to give ethyl 2-(oxetan-3-ylidene)acetate as a colourless viscous oil (815 mg, 79%).

Workup

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

Sources & evidence

ORD record
ord-bbd0e5333eeb448095c0475a488c5ea8
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

Loading…