Water → HCID 178472520, compound

Temperature

-30 °C

To a cooled (-30° C.) solution of ethyl 3-oxocyclobutanecarboxylate (J. Org. Chem. 1988, 53, 3481) (18.1 g, 130 mmol) in ethanol (100 ml) was added NaBH4 (4.92 g, 130 mmol) in small potions over 0.25 h. The reaction mixture was stirred at -30° C. for 0.5 h and then at room temperature for 0.5 h. The reaction mixture was poured into water (200 ml) and extracted with ether (500 ml). The organic phase was washed with brine (200 ml), dried (MgSO4) and concentrated. The residue was distilled to afford 15.1 g (81%) of ethyl cis-3-hydroxycyclobutanecarboxylate as a colorless oil: bp 86°-88° C. (1 mmHg); 1H NMR δ4.24 (m, 3H), 2.66-2.52 (m, 3H), 2.28-2,09 (m, 2H), 2.03 (br s, 1H), 1.26 (t, J=7.3 Hz, 3H).

1. waitat room temperature for 0.5 h
2. extractionextracted with ether (500 ml)
3. washThe organic phase was washed with brine (200 ml)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. distillationThe residue was distilled

ORD record

ord-af6d5148de7d4813acf295d57071a554

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05681858