Water → 2-Oxoethyl butyrate

HRID 323897Notes

Reaction equation

HRID 323897 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>[O:9]=[CH:8][CH2:7][O:6][C:1](=[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 butyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As a nonlimiting example using method C in FIG. 2, (5-oxo-1,3-oxathiolan-2-yl)methyl butanoate or the 5-acetyloxy derivative thereof may be obtained from process which includes reacting 2,2-diethoxyethyl butanoate in DCM and treating with TFA and water. This reaction yields 2-oxoethylbutanoate, which may be reacted with mercaptoacetic acid in CSA and DCM to produce the desired (5-oxo-1,3-oxathiolan-2-yl)methyl butanoate, or with 1,4-dithiane-2,5-diol in THF to obtain the 5-acetyloxy derivative.

Sources & evidence

ORD record
ord-f006308bb4a44ef4b851f51b9217cd05
Source dataset
uspto-grants-2001_04
Patent number
US06215004B1

Reaction notes

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