Sodium borohydride → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanol

HRID 2036597Notes

Reaction equation

HRID 2036597 reaction equation
[C:1]1([C:7]2[C:8]3[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=3[S:10][C:11]=2[C:12](=[O:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2[C:8]3[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=3[S:10][C:11]=2[CH:12]([OH:14])[CH3:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 104910361-(3-Phenylbenzo[b]thiophen-2-yl)ethanone

Product 1

HCID 584591571-(3-Phenylbenzo[b]thiophen-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(3-phenylbenzo[b]thiophen-2-yl)ethanone (430 mg, 1.704 mmol) dissolved in MeOH (5 mL) at rt was added sodium borohydride (0.093 mL, 2.64 mmol). After 5 min, no starting material remained. The reaction was partitioned between water and EtOAc, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine then stirred over MgSO4, filtered, and concentrated under reduced pressure to give 1-(3-phenylbenzo[b]thiophen-2-yl)ethanol as a colorless, crystalline solid: 1H NMR (400 MHz, CDCl3) δ 1.46 (d, J=6.3 Hz, 3H), 2.19 (br. s., 1H), 5.09 (q, J=6.5 Hz, 1H), 7.16-7.40 (m, 8H), 7.70-7.77 (m, 1H).

Workup

  1. customThe reaction was partitioned between water and EtOAc
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d0bcfc3231a40c685f932998511e190
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

Loading…