Hydrochloric Acid → Naphtho[1,2-b]furan-2-methanol

To a RB flask equipped with magnetic stirring bar, reflux condenser, N2 inlet line with bubbler was added ethyl naphtho[1,2-b]furan-2-carboxylate (H. G. Pars Pharmaceutical Laboratories, Inc., 6.85 g, 28.5 mmol), lithium borohydride (Aldrich, 0.62 g, 28.5 mmol) and dry THF (400 mL). The mixture was stirred at reflux for 6 h and then poured into H2O (1 L). The reaction mixture was acidified with 1N HCl and the resulting white solid was filtered, washed with additional H2O (500 mL) then dissolved in CH2CL2 (500 mL), dried (Na2SO4), filtered, concentrated to 200 mL and diluted to 500 mL with hexane. The resulting material was filtered, washed with hexane (100 mL), and placed in a vacuum oven overnight (80°) to give a total of 4.8 g (69.7%) of naphtho[1,2-b]furan-2-methanol, mp 105.5°-107°, (C,H).

1. customTo a RB flask equipped with magnetic stirring bar
2. temperaturereflux condenser, N2 inlet line with bubbler
3. temperatureat reflux for 6 h
4. filtrationthe resulting white solid was filtered
5. washwashed with additional H2O (500 mL)
6. dissolutionthen dissolved in CH2CL2 (500 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated to 200 mL
10. additiondiluted to 500 mL with hexane
11. filtrationThe resulting material was filtered
12. washwashed with hexane (100 mL)
13. customplaced in a vacuum oven overnight (80°)

ORD record

ord-d4d7506ce208480293e099244c1d0c73

Source dataset

uspto-grants-1990_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04970227