Hydrochloric Acid → (S)-1-(2-Furyl)-1-pentanol

Temperature

10 °C

10.4 mmol (10.4 mL) of diborane (1 M solution in THF) was added dropwise in a period of 10 m at room temperature to a solution of 2-valeryl furan (2.62 g, 17.2 mmol) and 1.68 mmol (4.2 mL) of (3aR)-1,3,3-triphenyl pyrrolidino [1,2-c] [1,3,2] oxazaborole (see E. J. Corey et al. J. Am. Chem. Soc. 1987, 109, 7925-26, 0.4M solution in THF) in 25 mL THF. The reaction mixture was stirred for 20 m and was cooled to 10° C. 6 mL methanol was cautiously added and followed by adding 62 mg HCl (by weight) in ether. Stirred for 0.5 h, white solid was precipitated out. The cloudy mixture was poured into 100 mL ether and 100 mL water. The organic layer was separated, washed with saturated sodium bicarbonate, water, brine, dried and filtered. The filtrate was evaporated to an yellowish oil which was chromatographed eluting with 10 % ethyl acetate in hexane to obtain 70% of the product. [α]25D =-13°, 60% ee by Mosher' ester analysis.

1. stirringStirred for 0.5 h
2. customwhite solid was precipitated out
3. additionThe cloudy mixture was poured into 100 mL ether and 100 mL water
4. customThe organic layer was separated
5. washwashed with saturated sodium bicarbonate, water, brine
6. customdried
7. filtrationfiltered
8. customThe filtrate was evaporated to an yellowish oil which
9. customwas chromatographed
10. washeluting with 10 % ethyl acetate in hexane

ORD record

ord-c3362f70087947e9a7caa72bda54863b

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05244910