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

HRID 395964

반응식

HRID 395964 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-faf6b4e969044f0c9c4870270a7ca141
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605618B2

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