Sodium borohydride → HCID 67341912, compound

HRID 1669314Notes

Reaction equation

HRID 1669314 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[N:13]=[CH:12][C:11]([C:14](=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[F:24][C:2]([F:1])([F:25])[C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[N:13]=[CH:12][C:11]([CH:14]([OH:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67342598HCID 67342598, compound

Product 1

HCID 67341912HCID 67341912, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1-[6-(4-Trifluoromethyl-phenoxy)-pyridin-3-yl]-heptan-1-one (1.45 g, 4.13 mmol) is dissolved into denatured ethanol (20 mL) at room temperature then cooled to 0° C. in an ice bath. Sodium borohydride (0.132 g, 4.13 mmol) is then carefully added in small portions. The reaction is allowed to warm slowly to room temperature and is monitored by HPLC. Upon complete consumption of starting material, the reaction is carefully quenched with water and diluted with ethyl acetate. The ethanol is removed and the residue is extracted with ethyl acetate, washed, dried, and concentrated. The 1-[6-(4-trifluoromethyl-phenoxy)-pyridin-3-yl]-heptan-1-ol (1.29 g, 3.65 mmol, 88%), is obtained in purified form after flash column chromatography.

Workup

  1. temperatureto warm slowly to room temperature
  2. customUpon complete consumption of starting material
  3. customthe reaction is carefully quenched with water
  4. additiondiluted with ethyl acetate
  5. customThe ethanol is removed
  6. extractionthe residue is extracted with ethyl acetate
  7. washwashed
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1401cd8aa98349798de00b350c13a8c2
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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