Sodium borohydride → HCID 57546211, compound

HRID 913905Notes

Reaction equation

HRID 913905 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:20]=[O:21])[C:6]2[N:10]=[N:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:7]=2[CH:19]=1.[BH4-].[Na+]>C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([CH2:20][OH:21])[C:6]2[N:10]=[N:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:18])[CH3:16])[C:7]=2[CH:19]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57546197HCID 57546197, compound

Product 1

HCID 57546211HCID 57546211, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d][1,2,3]triazole-4-carbaldehyde (165 mg, 0.478 mmol) in ethanol (5 mL) at 0° C. was added sodium borohydride (18.1 mg, 0.48 mmol). The ice bath was removed. After 15 min, the reaction was recooled to 0° C., quenched by the cautious addition of saturated ammonium chloride, and poured into ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 165 mg (99%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.67 (s, 1H), 6.02 (s, 2H), 5.30 (s, 2H), 3.70 (s, 1H), 3.56 (m, 2H), 0.89 (m, 2H), −0.09 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 145.6, 135.1, 132.3, 130.4 (q, J=33 Hz), 124.0 (q, J=273 Hz), 118.5 (q, J=2.9 Hz), 107.4 (q, J=4.8 Hz), 77.3, 67.6, 61.0, 17.7, −1.5.

Workup

  1. customThe ice bath was removed
  2. customwas recooled to 0° C.
  3. customquenched by the cautious addition of saturated ammonium chloride
  4. additionpoured into ether
  5. washThe ethereal was washed with water (2×)
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give 165 mg (99%) as a colorless oil

Sources & evidence

ORD record
ord-5f17a5e59e2a48e5a661bab33c607004
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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