Hydrochloric Acid → Cyclopentanecarboxylic acid, 3-hydroxy-, methyl ester

Temperature

23 °C

A solution of methyl 3-oxocyclopentanecarboxylate (9.58 g, 67.5 mmol) in THF (100 ml) was added to a slurry of sodium borohydride (3.8 g, 100 mmol) in THF (100 ml). The mixture was stirred at 23° C. for 2 h, cooled to 0° C. and acidified to pH 6 with 1M hydrochloric acid. The mixture was extracted with EtOAc (2×100 ml) and the organic extracts were washed with water and saturated sodium chloride (100 ml each). The extracts were dried and the solvent was evaporated in vacuo to give the title compound as a colorless liquid, 6.66 g (68% yield), (a mixture of two isomers); ir (liq.) νmax : 3450, 1725 cm-1 : 1Hmr (CDCl3) δ: 4.30 (m, 1H, H-3), 3.70-3.67 (2×s, 3H, OMe), 2.9 (m, 1H, H-1), 2.8 (s, 1H, OH) and 2.3-1.6 ppm (m, 6H, CH2).

1. temperaturecooled to 0° C.
2. extractionThe mixture was extracted with EtOAc (2×100 ml)
3. washthe organic extracts were washed with water and saturated sodium chloride (100 ml each)
4. customThe extracts were dried
5. customthe solvent was evaporated in vacuo

ORD record

ord-d92a0ed530ce44389ae954a51e0793c4

Source dataset

uspto-grants-1981_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04272437