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, 1 H, 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-f4199c12bf2e4140bcf8c83eaaf5ea54

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04378314