Sulfuryl chloride → Ethyl 2-chloro-3-oxopentanoate

HRID 1081648Notes

Reaction equation

[O:1]=[C:2]([CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:14])(=O)=O>>[Cl:14][CH:3]([C:2](=[O:1])[CH2:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Reactant 2

HCID 24648Sulfuryl chloride

HCID 78656Ethyl 3-oxovalerate

Product 1

HCID 12923424Ethyl 2-chloro-3-oxopentanoate

Procedure

Ethyl 3-oxopentanoate, 20.0 grams (0.175 mole), was stirred at ambient temperature, and 23.6 grams (0.175 mole) of sulfuryl chloride was added dropwise during a 20 minute period. Upon completion of addition, the reaction mixture was stirred for about 16 hours. The reaction mixture was then distilled under reduced pressure, yielding 23.3 grams of ethyl 2-chloro-3-oxopentanoate; bp 100°-103° C. at 21mm.

Workup

additionUpon completion of addition
distillationThe reaction mixture was then distilled under reduced pressure

Sources & evidence

ORD record: ord-ad2d4179a7754d1594081ac0fe95a47b
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05587379

Reaction notes

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