Thiophene → Cyclopentyl-2-thienylmethanone

HRID 1857804Notes

Reaction equation

HRID 1857804 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH:6]1([C:11](O)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:11]([CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:12]

Participants

4

Reactant 2

HCID 8030ThiopheneHCID 18840Cyclopentanecarboxylic acid

Product 1

HCID 10219686Cyclopentyl-2-thienylmethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.8 g (105 mmol, 1.2 equivs.) of thiophene and 10.0 g (88 mmol) of cyclopentanecarboxylic acid in 20 g of polyphosphoric acid was stirred at 75° C. for 2 hours. The reaction mixture was diluted with water and extracted with o-dichlorobenzene to afford 99% pure product (GC, area % analysis). The mixture was azeotropically dried by stripping a small portion of the solvent. The crude cyclopentyl 2-thienyl ketone solution was then used without purification, for the bromination step of Example 2.

Workup

  1. extractionextracted with o-dichlorobenzene

Sources & evidence

ORD record
ord-074707b8841643b8be6135fd211e64dc
Source dataset
uspto-grants-2000_11
Patent number
US06147226

Reaction notes

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