Oxalyl chloride → 2-(5-t-Butylthiophen-2-yl)-cyclopropanecarbonyl chloride

HRID 1252466Notes

Reaction equation

HRID 1252466 reaction equation
[C:1]([C:5]1[S:9][C:8]([CH:10]2[CH2:12][CH:11]2[C:13]([OH:15])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:19])=O>CCCCCC>[C:1]([C:5]1[S:9][C:8]([CH:10]2[CH2:12][CH:11]2[C:13]([Cl:19])=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 201399602-(5-t-Butylthiophen-2-yl)-cyclopropanecarboxylic acid

Product 1

HCID 201399582-(5-t-Butylthiophen-2-yl)-cyclopropanecarbonyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 2-(5-t-butylthiophen-2-yl)-cyclopropanecarboxylic acid (3.38 g, 0.015 mol) and oxalyl chloride (2.65 g, 0.021 mol) in hexane (35 ml) was stirred at room temperature for 2 hours and then warmed at 60° C. for 3 hours. The hexane and excess oxalyl chloride were removed in vacuo to give 2-(5-t-butylthiophen-2-yl)-cyclopropanecarbonyl chloride (3.59 g, 99%) as a pale yellow liquid which was used in the next stage without further purification.

Workup

  1. temperaturewarmed at 60° C. for 3 hours
  2. customThe hexane and excess oxalyl chloride were removed in vacuo

Sources & evidence

ORD record
ord-4e2b07b47cbc4f229417953df664b060
Source dataset
uspto-grants-1988_05
Patent number
US04743602

Reaction notes

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