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

To a RB flask equipped with magnetic stirring bar, reflux condenser and N2 inlet tube with bubbler was added ethyl phenanthro[1,2-b]furan-2-carboxylate (H. G. Pars Pharmaceutical Laboratories, Inc., 7.9 g, 27.2 mmol), lithium borohydride (Aldrich, 0.65 g, 30 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 (1500 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. A total of 6.1 g (90.1%) of phenanthro[1,2-b]-furan-2-methanol, mp 125°-126° , was obtained (C,H).

1. customTo a RB flask equipped with magnetic stirring bar
2. temperaturereflux condenser and N2 inlet tube with bubbler
3. temperatureat reflux for 6 h
4. filtrationthe resulting white solid was filtered
5. washwashed with additional H2O (1500 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

ORD record

ord-61e93e598362434f9130f8b2ebef0276

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04999369