Oxalyl chloride → (1S,2S)-2-phenylcyclopropane-1-carbonyl chloride

HRID 1256289Notes

Reaction equation

HRID 1256289 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]1([C@H:13]2C[C@@H:14]2C(O)=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[C:7]1([C@H:13]2[CH2:14][C@@H:1]2[C:2]([Cl:4])=[O:3])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 7785172-Phenyl-1-cyclopropanecarboxylic acid, (1S-trans)-

Product 1

HCID 7005116(1S,2S)-2-phenylcyclopropane-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry 100 ml round-bottomed flask was added oxalyl chloride (2.0 ml, 23 mmol) to 8B (0.25 g, 1.5 mmol) in CH2Cl2 at room temperature to give a yellow solution. In 2.5 hours, the reaction was complete. The crude mixture was concentrated in vacuo and residual TFA was removed azeotropically with toluene 3 times to give the desired product (1S,2S)-2-phenylcyclopropanecarbonyl chloride (8B-1), which was used in the next step without further purification.

Workup

  1. customto give a yellow solution
  2. concentrationThe crude mixture was concentrated in vacuo and residual TFA
  3. customwas removed azeotropically with toluene 3 times

Sources & evidence

ORD record
ord-3f9521c0b0724a6cbf788296d871c42d
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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