Benzyl 2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)acetate → Benzyl 2-oxo-2-(tetrahydro-2H-pyran-4-yl)acetate

HRID 516887ノート

反応式

HRID 516887 の反応式
[OH:1][CH:2]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]>ClCCl>[O:1]=[C:2]([CH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

参加物

3

反応物 1

HCID 90185045Benzyl 2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)acetate

生成物 1

HCID 90184979Benzyl 2-oxo-2-(tetrahydro-2H-pyran-4-yl)acetate収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A Dess-Martinn reagent (5.7 g, 13.44 mmol) was added to a solution of benzyl 2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)acetate (2.1 g, 8.404 mmol) in dichloromethane (50 ml) at room temperature, and the mixture was stirred for 15 hr. The reaction mixture was quenched with 10% sodium thiosulfate and was extracted with dichloromethane. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine and was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=9:1) to give the title compound as a light yellow oil (1.8 g, yield 90%).

後処理

  1. customThe reaction mixture was quenched with 10% sodium thiosulfate
  2. extractionwas extracted with dichloromethane
  3. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-0f5f6ed958ac4c1c963522207fc6ebc9
出典データセット
uspto-grants-2015_08
特許番号
US09115079B2

反応ノート

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