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

HRID 1359247Notes

Reaction equation

HRID 1359247 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-843ae46b6b214c2382f275f8e9d40acb
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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