Sodium borohydride → HCID 57546050, compound

HRID 913901Notes

Reaction equation

HRID 913901 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:20]=[O:21])[C:6]2[CH:7]=[CH:8][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:10]=2[CH:11]=1.[BH4-].[Na+]>CO>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])=[C:5]([CH2:20][OH:21])[CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 575460536-(Trifluoromethyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indole-4-carboxaldehyde

Product 1

HCID 57546050HCID 57546050, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-4-carbaldehyde (0.95 g, 2.77 mmol) in methanol (20 ml) at 25° C. was treated with sodium borohydride (0.209 g, 5.53 mmol) and stirred for 1 h. The resulting solution was concentrated in vacuo, taken up in ethyl acetate, washed with brine, dried over sodium sulfate and re-concentrated to a light yellow oil. Column chromatography (ethyl acetate/hexanes gradient elution) afforded 0.91 g (95%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ ppm 7.74 (s, 1H), 7.41 (m, 2H), 6.73 (m, 1H), 5.46 (s, 2H), 5.10 (s, 2H), 3.46 (m, 2H), 0.88 (m, 2H), −0.07 (s, 9H). Mass spec.: 346.17 (MH)+.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationre-concentrated to a light yellow oil
  5. washColumn chromatography (ethyl acetate/hexanes gradient elution)
  6. customafforded 0.91 g (95%) as a colorless oil

Sources & evidence

ORD record
ord-13691e3dc70f4dcb93fe6df50f32b259
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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