Methanol → Methyl 2-cyclopentylacetate

HRID 1684517Notes

Reaction equation

HRID 1684517 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]1

Participants

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

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed with a 5% sodium bicarbonate solution (50 ml), water (50 ml) and brine (50 ml)
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2eb7ba746cb34bf8a8874e215a7fea5e
Source dataset
uspto-grants-1997_06
Patent number
US05641775

Reaction notes

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