Dichloromethane → Propionyloxyacetyl chloride

HRID 39254Notes

Reaction equation

HRID 39254 reaction equation
S(Cl)(Cl)=[O:2].C(=O)(O[CH2:10][O:11][C:12](=[O:15])[CH2:13][CH3:14])SCC.[CH2:17]([Cl:19])Cl>>[C:12]([O:11][CH2:10][C:17]([Cl:19])=[O:2])(=[O:15])[CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 14800950O-Propanoyloxymethyl S-Ethyl Carbonothioate

Product 1

HCID 11252105Propionyloxyacetyl chlorideYield 100%

Procedure

Thionyl chloride (101 μL, 1.25 mmol) was added drop-wise to a solution of 53 (160 mg, 0.832 mmol) in CH2Cl2 (0.5 mL) at 0° C. then the solution was stirred for a further 1.5 hr. The solvent was removed under reduced pressure resulting in the volatile chloroformate 54 (138 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 1.18 (t, J=7.4, 3H), 2.45 (q, J=7.4, 2H), 5.83 (s, 2H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fa376d4a030d486f8a0a3fc9721affc8
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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