Sodium borohydride → Ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate

HRID 590958Notes

Reaction equation

HRID 590958 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]>CO.O1CCCC1>[OH:3][CH:4]([C:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70813788Ethyl 2-oxo-2-(2-phenyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 70813709Ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetateYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (53 mg, 1.40 mmol) was added to a solution of ethyl 2-oxo-2-(2-phenyl-1-benzothiophen-3-yl)acetate (2b) (430 mg, 1.38 mmol) in a mixture of methanol (10 mL) and tetrahydrofuran (5 mL) under a nitrogen atmosphere. The reaction mixture was stirred for 1 hour, quenched with water (2 mL) and concentrated in vacuo. The residue was diluted with dichloromethane (20 mL), washed with water (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (dichloromethane/ethanol 99/1) to afford the desired alcohol (2c) as a white solid (190 mg, 0.60 mmol, 44%).

Workup

  1. customquenched with water (2 mL)
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with dichloromethane (20 mL)
  4. washwashed with water (2×10 mL), brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography on silica gel (dichloromethane/ethanol 99/1)

Sources & evidence

ORD record
ord-7cbe37588f2844319fad41c801d90d2d
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

Loading…