Tetrahydrofuran → 4-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol

HRID 416141노트

반응식

HRID 416141 반응식
[OH:1][C:2]1([CH2:8][O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[CH:18]=3)=[C:12]([CH3:25])[CH:11]=2)[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.O1CCCC1.[BH4-].[Na+]>CO>[OH:24][CH2:23][C:19]1[CH:18]=[C:17]([C:13]2[C:12]([CH3:25])=[CH:11][C:10]([O:9][CH2:8][C:2]3([OH:1])[CH2:7][CH2:6][S:5][CH2:4][CH2:3]3)=[CH:15][C:14]=2[CH3:16])[CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 231574564'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-carbaldehyde

생성물 1

HCID 231571864-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol수율 88%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4′-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-carbaldehyde (2.12 g, 5.95 mmol) in a mixed solvent of tetrahydrofuran (8 mL) and methanol (4 mL) was added sodium borohydride (0.225 g, 5.95 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 20 min. The reaction solution was concentrated under reduced pressure, aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (1.87 g, yield 88%) as colorless crystals.

후처리

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure, aqueous ammonium chloride solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b793a6ff7b2345eb9180afca105fbcf2
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088821B2

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