Tetrahydrofuran → 4-Hydroxy-4'-(1-hydroxyethyl)biphenyl

HRID 1587586노트

반응식

HRID 1587586 반응식
C(O[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.[O:18]1CC[CH2:20][CH2:19]1.[BH4-].[Na+]>CO>[OH:18][CH:19]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)[CH3:20]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 144384094-Methylcarbonyloxy-4'-hydroxybiphenyl

생성물 1

HCID 139308004-Hydroxy-4'-(1-hydroxyethyl)biphenyl수율 92.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution containing 4-acetoxy-4'-hydroxy-1,1'-biphenyl from part A (5.0 g, 23.6 mmol) in methanol (500 mL) and tetrahydrofuran (30 mL) is treated with sodium borohydride (0.9 g, 23.8 mmol) in portions over 30 minutes at room temperature. After 2 hours, the reaction mixture is concentrated under reduced pressure, diluted with water (400 mL), acidified with 2N HCl and extracted with ethyl acetate. The organic layer is washed with water and brine, dried over MgSO4 and concentrated to a solid residue. Crystallization of the solid from ethyl acetate gives 4.7 g (92.9%) of the title compound, m.p. 159°-160° C.; MS (EI m/z): 214 (M)+ and 199 (b.p. M--CH3)+.

후처리

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additiondiluted with water (400 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a solid residue
  7. customCrystallization of the solid from ethyl acetate

출처 및 근거

ORD 기록
ord-300177ea7ab14f11b5bd5c26b0c9fdb8
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05218124

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