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

HRID 606962

反応式

HRID 606962 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 66631792trans-2-Benzhydryl-tetrahydropyran-4-ol収率 68%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-13dce756e4584642b572d9229e9ad2c4
出典データセット
uspto-grants-2011_03
特許番号
US07915433B2

関連ノート

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