Sodium borohydride → HCID 58026159, compound

HRID 2387329Notes

Reaction equation

HRID 2387329 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:17])([CH3:16])[CH2:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12].[BH4-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:17])([CH3:16])[CH2:9][CH:10]([OH:15])[C:11]([F:13])([F:14])[F:12]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58026165HCID 58026165, compound

Product 1

HCID 58026159HCID 58026159, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask was added 4-(2-bromophenyl)-1,1,1-trifluoro-4-methylpentan-2-one (3.0 g, 9.7 mmol) in 70 mL of MeOH and 70 mL of THF at 0° C., followed by the slow addition of NaBH4 (1.1 g, 29.1 mmol). The reaction mixture was stirred at room temperature for 24 hours and then concentrated in vacuo. The residue was diluted with 1000 mL of ethyl acetate, washed with 200 mL of saturated aqueous sodium bicarbonate solution, 200 mL of brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography. The column was eluted with 0-20% EtOAc/hexanes to afford 1.76 g (58%) of 4-(2-bromophenyl)-1,1,1-trifluoro-4-methylpentan-2-ol.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with 1000 mL of ethyl acetate
  3. washwashed with 200 mL of saturated aqueous sodium bicarbonate solution, 200 mL of brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified by flash chromatography
  8. washThe column was eluted with 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-17dd414f32044b59bc265f9f8bde692a
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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