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

HRID 1359247ノート

反応式

HRID 1359247 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-843ae46b6b214c2382f275f8e9d40acb
出典データセット
uspto-grants-2003_07
特許番号
US06599925B2

反応ノート

読み込み中…