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

HRID 706528Notes

Reaction equation

HRID 706528 reaction equation
[Cl:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:8](OCC)=[O:9].CC(C)([O-])C.[K+:18]>C(OC(C)C)(C)C>[Cl:1]/[C:2](/[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:8]/[O-:9].[K+:18]

Participants

5

Reactant 3

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

Product 1

HCID 23711836Potassium (E)-2-chloro-3-ethoxy-3-oxoprop-1-en-1-olateYield 79.4%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of ethyl 2-chloroacetate (220.8 g; 1802 mmol) and ethyl formate (133.5 g; 1802 mmol) was added slowly to a suspension of potassium t-butoxide (202.2 g; 1802 mmol) in diisopropyl ether (2000 mL) at 0° C. (maintaining the temperature <20° C.) with mechanical stirring. The mixture was stirred at ambient temperature for 24 hours. The solids were collected by filtration and washed with diisopropyl ether (500 mL) and acetonitrile (2×1500 mL). The material was dried under vacuum to give the product (270 g) which was used without further purification.

Workup

  1. temperaturemaintaining the temperature <20° C.) with mechanical stirring
  2. filtrationThe solids were collected by filtration
  3. washwashed with diisopropyl ether (500 mL) and acetonitrile (2×1500 mL)
  4. customThe material was dried under vacuum

Sources & evidence

ORD record
ord-de9792b2f47f447584e24fc916a1f61b
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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