Dimethylformamide → rel-(1R,2R)-cyclopropane-1,2-dicarbonyl dichloride

HRID 1504816Notes

Reaction equation

[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C@@H:7]1(C(O)=O)C[C@H:8]1[C:10]([OH:12])=O.CN(C=O)C.[Cl:21]CCl>>[C@@H:1]1([C:2]([Cl:4])=[O:3])[CH2:7][C@H:8]1[C:10]([Cl:21])=[O:12]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6344Dichloromethane

HCID 65578Oxalyl chloride

HCID 69504501,2-Cyclopropanedicarboxylic acid, trans-

Product 1

HCID 12678481rel-(1R,2R)-cyclopropane-1,2-dicarbonyl dichloride

Procedure

Oxalyl chloride (112.0 mL, 1.153 mol) was added drop-wise to a stirred solution of rel-(1R,2R)-cyclopropane-1,2-dicarboxylic acid (60.0 g, 0.461 mol) in dichloromethane (600 mL) at 0° C. DMF (2 mL) was added to the reaction mixture at 0° C., and then the reaction mixture was allowed to warm to ambient temperature. After 2 hours, the reaction mixture was concentrated under reduced pressure to afford rel-(1R,2R)-cyclopropane-1,2-dicarbonyl dichloride. The material was used without further purification.

Workup

concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-8202079c5e2547e8b4dc6d08e14932f4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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