Methanol → Methyl 2-cyclopentylacetate
Reaction equation
S(Cl)(Cl)=O.[CH:5]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:14]O>>[CH:5]1([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1Participants
4
Procedure
Thionyl chloride (7.0 ml) was slowly added to a solution of cyclopentylacetic acid (8.0 ml) in dry methanol (60 ml) and the mixture was stirred at 23° for 20 h. The mixture was concentrated in vacuo; then, the residue was taken up in DCM (100 ml), washed with a 5% sodium bicarbonate solution (50 ml), water (50 ml) and brine (50 ml), dried and concentrated in vacuo to give the title compound (6.47 g) as a yellow oil, which was not purified further. T.l.c. CH-EA (1:1), Rf =0.79. 1H-NMR: 3.70(s); 2.35(s); 2.4-2.15(m); 1.8(m); 1.7-1.5(m); 1.2(m).
Workup
- concentrationThe mixture was concentrated in vacuo
- washwashed with a 5% sodium bicarbonate solution (50 ml), water (50 ml) and brine (50 ml)
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2eb7ba746cb34bf8a8874e215a7fea5e
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05641775
Reaction notes
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