Sodium borohydride → 2-Cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanol

HRID 1359213Notes

Reaction equation

HRID 1359213 reaction equation
[CH:1]1([CH2:6][C:7]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=3)[CH:19]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([CH2:6][CH:7]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]=2[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=3)[CH:19]=2)[OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 181828082-Cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanone

Product 1

HCID 181828152-Cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanolYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanone (2.03 g, 5.28 mmol) in ethanol (25 mL) cooled in an ice bath was added sodium borohydride (1.05 g, 27.7 mmol) in three portions. The reaction mixture was stirred for about 18 hours at room temperature and then concentrated. The residue was partitioned in warm ethyl acetate and water. The organic phase was washed with water and brine. It was dried over anhydrous magnesium sulfate, filtered and concentrated to afford 2-cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanol as a cream-colored solid (1.84 g), mp 176-177° C. 1HNMR (200 MHz, DMSO-d6): δ8.2 (s, 1H), 7.8-8.0 (m, 4H), 7.6 (d, 1H, J=7.5 Hz), 7.2-7.45 (m, 4H), 5.4 (s, 1H), 5.1-5.2 (br, 1H), 3.9 (s, 3H), 1.95-2.15 (br m, 1H), 1.8-1.95 (br m, 2H), 1.2-1.6 (br m, 4H), and 1.0-1.2 ppm (br m, 2H).

Workup

  1. temperaturecooled in an ice bath
  2. concentrationconcentrated
  3. customThe residue was partitioned in warm ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialIt was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-baaaf9b00337478588fddc44de1c9edb
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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