Water → 2-Oxoethyl butyrate

HRID 495672Notes

Reaction equation

HRID 495672 reaction equation
[C:1]([O:6][CH2:7][CH:8](OCC)[O:9]CC)(=[O:5])[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[C:1]([O:6][CH2:7][CH:8]=[O:9])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 112641752,2-diethoxyethyl Butanoate

Product 1

HCID 98988312-Oxoethyl butyrateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A well-stirred solution of 28 (8.16 g, 40 mmol) in DCM (200 ml) at room temperature, was treated with TFA (44.4 g, 30 ml, 390 mmol) and water (7.2 g, 7.2 ml, 400 mmol). After stirring for 2 hours at room temperature the solution was evaporated at 35° C. It was then coevaporated with hexane several times to remove traces of TFA. Compound 24 (5.2 g, 40 mmol, 100%) was obtained as a colorless liquid, and was used in the next step without any further purification. Synthesis of (5-oxo-1,3-oxathiolan-2-yl) methyl butanoate (25)

Workup

  1. customwas evaporated at 35° C
  2. customto remove traces of TFA

Sources & evidence

ORD record
ord-0981da42c69c41d49bcc4018209a30e1
Source dataset
uspto-grants-2005_09
Patent number
US06939965B2

Reaction notes

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