Water → HCID 13477890, compound

HRID 371034Notes

Reaction equation

HRID 371034 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:26]=[CH:25][C:13]([O:14][CH:15]([CH3:24])[C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[BH4-].[Na+].O.C(Cl)Cl>C(O)C>[F:27][C:2]([F:1])([F:28])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:26]=[CH:25][C:13]([O:14][CH:15]([CH3:24])[CH:16]([OH:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=2)=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 13477889HCID 13477889, compound

Product 1

HCID 13477890HCID 13477890, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]-3-oxopentanoate (175 mg, 0.44 mmol) in 5 ml of absolute ethanol at 0° is added sodium borohydride (32 mg, 0.84 mmol). The mixture is stirred for 15 minutes, after which it is poured into water and methylene chloride. The aqueous phase is separated and back-extracted with methylene chloride. The combined solvent extracts are washed with brine and dried. Solvent is removed by rotoevaporation, and the residue is purified by prep. thin layer chromatography (silica gel, 25% ethyl acetate/hexane) to yield ethyl 4-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]-3-hydroxypentanoate.

Workup

  1. customThe aqueous phase is separated
  2. extractionback-extracted with methylene chloride
  3. washThe combined solvent extracts are washed with brine
  4. customdried
  5. customSolvent is removed by rotoevaporation
  6. customthe residue is purified by prep

Sources & evidence

ORD record
ord-b1802991bbcf48d1aa9d5836e763db8a
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Reaction notes

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