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

HRID 2351488Notes

Reaction equation

HRID 2351488 reaction equation
[CH:1]1[C:2]2[CH:22]=[CH:21][C:20]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH:13]=[CH:12][C:11]=3[C:3]=2[O:4][C:5]=1[C:6](OCC)=[O:7].[BH4-].[Li+].C1COCC1.Cl>O>[CH:1]1[C:2]2[CH:22]=[CH:21][C:20]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH:13]=[CH:12][C:11]=3[C:3]=2[O:4][C:5]=1[CH2:6][OH:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 12274414Ethyl phenanthro(1,2-b]furan-2-carboxylate

Product 1

HCID 14770239Phenanthro[1,2-b]furan-2-methanolYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a RB flask equipped with magnetic stirring bar, reflux condenser, 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 1 N 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).

Workup

  1. customTo a RB flask equipped with magnetic stirring bar
  2. temperaturereflux condenser, 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

Sources & evidence

ORD record
ord-2824ef337b944ad7ac5fadee2bf0cbd7
Source dataset
uspto-grants-1989_10
Patent number
US04873258

Reaction notes

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