Dimethylformamide → Cyclopentyl-phenyl-acetyl chloride

HRID 722715Notes

Reaction equation

HRID 722715 reaction equation
[C:1]1([CH:7]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.C(Cl)(=O)C([Cl:24])=O>C(Cl)Cl>[C:1]1([CH:7]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]([Cl:24])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 980142-Cyclopentyl-2-phenylacetic acid

Product 1

HCID 12573274Cyclopentyl-phenyl-acetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of α-phenylcyclopentaneacetic acid (422 mg; 2.0 mmol) and a catalytic amount of dry dimethylformamide (ca. 20 uL) in 5 mL of dry methylene chloride under nitrogen at room temperature was added oxalyl chloride (1.5 mL of 2.0 M solution in methylene chloride) dropwise. After 45 minutes, the mixture was concentrated in vacuo to give crude α-phenylcyclopentaneacetyl chloride which was used immediately for Step 2.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-4f1fd02f747d46fbb64e7a0461c141d0
Source dataset
uspto-grants-2006_11
Patent number
US07138529B2

Reaction notes

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