Monobenzone → (2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxirane

HRID 395964

反応式

HRID 395964 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:29][C@H:30]2[O:32][CH2:31]2)(=O)=O)=CC=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:29][C@@H:30]2[CH2:31][O:32]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

生成物 1

HCID 11817709(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxirane収率 71.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

4-Benzyloxyphenol (15.00 g, 74.91 mmol) in anhydrous N,N-dimethylformamide (50 mL) was added to a solution of sodium hydride (60% dispersion in oil) (2.88 g, 74.9 mmol) in N,N-dimethylformamide (50 mL). The solution was stirred for 30 minutes and (S)-(+)-glycidyl 4-methylbenzenesulfonate (17.12, 75.0 mmol) was added. The mixture was heated to 80° C. for 2 hours. The solvent was removed and the residue partitioned between diethyl ether and water. The organic phase was washed with brine-and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo. To yield the title compound as a white solid (13.6 g, 53.3 mmol).

後処理

  1. customThe solvent was removed
  2. customthe residue partitioned between diethyl ether and water
  3. washThe organic phase was washed with brine-
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent evaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-faf6b4e969044f0c9c4870270a7ca141
出典データセット
uspto-grants-2003_08
特許番号
US06605618B2

関連ノート

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