Lithium borohydride → 2,3-Dihydro-1-[(4-methoxy-2,6-dimethylphenyl)sulfonyl]-1H-indole-6-methanol

HRID 1808373Notes

Reaction equation

HRID 1808373 reaction equation
[BH4-].[Li+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24](OC)=[O:25])[CH:22]=3)[CH2:17][CH2:16]2)(=[O:14])=[O:13])=[C:7]([CH3:28])[CH:6]=1>C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH3:28])[C:8]([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][OH:25])[CH:22]=3)[CH2:17][CH2:16]2)(=[O:13])=[O:14])=[C:9]([CH3:11])[CH:10]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 59483781HCID 59483781, compound

Product 1

HCID 594838092,3-Dihydro-1-[(4-methoxy-2,6-dimethylphenyl)sulfonyl]-1H-indole-6-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (0.232 g, 0.0107 mol) was added at 0° C., under argon, to a solution of methyl 1-(4-methoxy-2,6-dimethylphenylsulfonyl)indoline-6-carboxylate (1 g, 0.0027 mol) in dry THF (30 ml), and the resulting reaction mixture was refluxed for 2 h. The solvent was removed in vacuo, water was added to the residue, and extraction with ethyl acetate was carried out. The organic phase was washed with water and saturated sodium chloride solution, then dried (Na2SO4) and concentrated in vacuo. The resulting crude product was used in the next stage without further purification. Yield: 0.9 g (97%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 2 h
  3. customThe solvent was removed in vacuo, water
  4. additionwas added to the residue, and extraction with ethyl acetate
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was used in the next stage without further purification

Sources & evidence

ORD record
ord-c88331edf60d433f910adda3a733198c
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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