Sodium borohydride → 2,2-dimethyl-1,1-dioxo-2,3-dihydro-1H-1lambda*6*-benzo[b]thiophen-3-ol

HRID 2089505Notes

Reaction equation

HRID 2089505 reaction equation
[CH3:1][C:2]1([CH3:14])[S:6](=[O:8])(=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[C:3]1=[O:13].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:14])[S:6](=[O:8])(=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[CH:3]1[OH:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 110310922,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide

Product 1

HCID 126307682,2-dimethyl-1,1-dioxo-2,3-dihydro-1H-1lambda*6*-benzo[b]thiophen-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,2-dimethyl-1,1-dioxo-1,2-dihydro-llambda*6*-benzo[b]thiophen-3-one (240 mg, 1.14 mmol) in ethanol (30 mL) at 0° C. is added NaBH4 (43 mg, 1.14 mmol). The reaction is placed at room temperature and permitted to stir for one hour. The reaction is quenched with saturated aqueous NH4Cl, and concentrated to near dryness. The resulting residue is diluted with ethyl acetate and washed with brine, dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:0) to provide 2,2-dimethyl-1,1-dioxo-2,3-dihydro-1H-1lambda*6*-benzo[b]thiophen-3-ol; MS: (ESI) m/z 213 (M+H)+.

Workup

  1. customis placed at room temperature
  2. customThe reaction is quenched with saturated aqueous NH4Cl
  3. concentrationconcentrated
  4. additionThe resulting residue is diluted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:0)

Sources & evidence

ORD record
ord-d5a9b005e5644d91ab1f003027012cb8
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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