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

HRID 1165646

반응식

HRID 1165646 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-abb1e924a370437bba764777d23bab25
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910218

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