thiirane (E)-ethyl 7-(thiiran-2-yl)hept-6-enoate → Ethyl 5-(2,5-dihydrothiophen-2-yl)pentanoate

HRID 1952328Notes

Reaction equation

HRID 1952328 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]1[CH2:13][S:12]1)[CH3:2].S1CC1>C1C=CC=CC=1>[S:12]1[CH2:13][CH:11]=[CH:10][CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14]

Participants

3

Reactant 1

HCID 86630496thiirane (E)-ethyl 7-(thiiran-2-yl)hept-6-enoate

Product 1

HCID 16070980Ethyl 5-(2,5-dihydrothiophen-2-yl)pentanoateYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of thiirane (E)-ethyl 7-(thiiran-2-yl)hept-6-enoate (40 mg, 0.19 mmol) and Cu(hfacac)2 (4.7 mg, 10 μmol) in benzene (20 mL) was heated at 120° C. for 1.5 h in a pressure tube. Concentration of the solvent in vacuo afforded a residue, which was purified by column chromatography (n-pentane) to give Ethyl 5-(2,5-dihydrothiophen-2-yl)pentanoate (32 mg, 80%) as a colorless oil.

Workup

  1. customConcentration of the solvent in vacuo afforded a residue, which
  2. customwas purified by column chromatography (n-pentane)

Sources & evidence

ORD record
ord-389dec8c884e495fa9090ffecdf6d2af
Source dataset
uspto-grants-2013_03
Patent number
US08404872B2

Reaction notes

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