Oxalyl chloride → trans-2-Phenyl-1-cyclopropanecarbonyl chloride

HRID 1409129Notes

Reaction equation

HRID 1409129 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 237413trans-2-Phenylcyclopropanecarboxylic acid

Product 1

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry 250 ml round-bottomed flask was added oxalyl chloride (0.90 ml, 1.8 mmol) to 8A (0.60 g, 3.5 mmol) in CH2Cl2 at room temperature to give a yellow solution. In 2 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 (1R,2R)-2-phenylcyclopropanecarbonyl chloride (8A-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-83149511e0fe4385a6917755d1bf8c45
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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