Sodium borohydride → 1-[2-(6-Methoxy-naphthalen-2-yl)-benzofuran-3-yl]-pentan-1-ol

HRID 1359247노트

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HRID 1359247 반응식
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]1[O:16][C:17]3[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=3[C:19]=1[C:20](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:9]=[CH:8]2>C(O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]1[O:16][C:17]3[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=3[C:19]=1[CH:20]([OH:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:9]=[CH:8]2

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 113372811-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

생성물 1

HCID 181827861-[2-(6-Methoxy-naphthalen-2-yl)-benzofuran-3-yl]-pentan-1-ol수율 92.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium borohydride ((7.56 g, 200 mmol) was added portion-wise to the stirring mixture of 1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (17.9 g, 50 mmol) in ethanol (600 mL). The mixture was stirred at room temperature for 2 hours then filtered. The solids were dissolved in methylene chloride and 2N hydrochloric acid solution. The organic phase was washed with water, dried over anhydrous magnesium sulfate and solvent evaporated to give the title compound (16.6 g). 1HNMR (300 MHz, DMSO-d6): δ8.2 (s, 1H), 7.98-7.92 (m, 2H), 7.9-7.82 (m, 2H) 7.62 (d, 1H, J=7.5 Hz), 7.38 (s, 1H), 7.35-7.22 (m, 3H), 5.46 (d, 1H, J=3.6 Hz), 5.15-5.07 (m, 1H), 3.92 (s, 3H), 2.12-1.97 (m, 1H), 1.95-1.82 (m, 1H), 1.44-1.21 (m, 3H), and 0.69 ppm (t, 3H, J=7.4 Hz).

후처리

  1. filtrationthen filtered
  2. dissolutionThe solids were dissolved in methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate and solvent
  5. customevaporated

출처 및 근거

ORD 기록
ord-843ae46b6b214c2382f275f8e9d40acb
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599925B2

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