Dimethylformamide → 3-Methyl-2-phenylvaleryl chloride

HRID 722712

Reaction equation

HRID 722712 reaction equation
[CH3:1][CH:2]([CH2:13][CH3:14])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4](O)=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl>[CH3:1][CH:2]([CH2:13][CH3:14])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([Cl:23])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2959613-Methyl-2-phenylpentanoic acid

Product 1

HCID 218860263-Methyl-2-phenylvaleryl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-methyl-2-phenylvaleric acid (1.23 g; 6.2 mmol) and a catalytic amount of dry dimethylformamide (ca. 20 μL) in 5 mL of dry methylene chloride under nitrogen at room temperature was added oxalyl chloride (4.8 mL of 2.0 M solution in methylene chloride) dropwise. After 45 minutes, the mixture was concentrated in vacuo and used immediately for Step 2.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-2a4c185e9436403caedbe74555c00be8
Source dataset
uspto-grants-2006_11
Patent number
US07138529B2

Linked notes

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