Boron trifluoride etherate → trans-2-Benzhydryl-tetrahydropyran-4-ol

HRID 78888

반응식

HRID 78888 반응식
[BH3-]C#N.[Na+].[CH:5]([CH:18]1[CH2:23][C:22](=[O:24])[CH:21]=[CH:20][O:19]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.B(F)(F)F.CCOCC>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH:5]([C@H:18]1[CH2:23][C@H:22]([OH:24])[CH2:21][CH2:20][O:19]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 8000Boron trifluoride etherateHCID 5003444Sodium cyanoborohydrideHCID 666308482-Benzhydryl-2H-pyran-4(3H)-one

생성물 1

HCID 66631792trans-2-Benzhydryl-tetrahydropyran-4-ol수율 68%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
-78 °C

실험 절차

NaCNBH3 (0.75 g, 12 mmol) was added portionwise to a mixture of 2-diphenylmethyl-2,3-dihydro-4H-pyran-4-one 2 (1.05 g, 4 mmol) and boron trifluoride etherate (1.99 g, 14 mmol) in dry THF (50 ml) cooled to −78° C. The reaction mixture was allowed to reach room temperature and the reaction was quenched with saturated aqueous NaHCO3 (30 ml). The organic phase was separated, and the aqueous phase was extracted with ethyl ether (3×20 ml). The organic phases were combined and dried over anhydrous Na2SO4. Removal of the solvent under reduced pressure, and purification by flash chromatography (hexane/ethyl acetate 7:3) first afforded trans-2-benzhydryl-tetrahydropyran-4-ol 3a (0.73 g, 68% yield).

후처리

  1. customto reach room temperature
  2. customthe reaction was quenched with saturated aqueous NaHCO3 (30 ml)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethyl ether (3×20 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-ec2926626b8f419e84c676de1793e7c2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841464B2

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