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

HRID 1252472Notes

Reaction equation

HRID 1252472 reaction equation
[C:1]([C:5]1[O: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[O: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 201399622-(5-t-Butylfuran-2-yl)-cyclopropanecarboxylic acid

Product 1

HCID 201399472-(5-t-Butylfuran-2-yl)-cyclopropanecarbonyl chlorideYield 101.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 2-(5-t-butylfuran-2-yl)-cyclopropanecarboxylic acid (3.6 g, 0.017 mol) and oxalyl chloride (4.4 g, 0.035 mol) in hexane (40 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-butylfuran-2-yl)-cyclopropanecarbonyl chloride (3.9 g, 100%) 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-d08a45b09c16472e88b16f654b30e951
Source dataset
uspto-grants-1988_05
Patent number
US04743602

Reaction notes

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