Ethyl chloroacetate → Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate

HRID 930996Notes

Reaction equation

HRID 930996 reaction equation
C[C:2](C)([O-:4])C.[K+:6].[Cl:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C(OCC)=O>>[Cl:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:2][O-:4].[K+:6]

Participants

4

Reactant 3

HCID 7751Ethyl chloroacetateHCID 8025Ethyl formateHCID 23665647Potassium tert-butoxide

Product 1

HCID 74089075Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olateYield 67.3%

Procedure

To a suspension of potassium tert-butoxide (5.2 g) in IPE (50 mL) were added ethyl 2-chloroacetate (5.6 g) and ethyl formate (3.4 g) under ice-cooling, and the mixture was stirred overnight at room temperature. The precipitate was collected by filtration, and dried to give the title compound (5.8 g). 1H NMR (300 MHz, DMSO-d6) δ 1.11 (3H, t, J=7.2 Hz), 3.92 (2H, q, J=7.2 Hz), 8.95 (1H, brs).

Workup

  1. temperaturecooling
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-ffb6d8f60a62411da880ef68c9c7a295
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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