Ethyl Acetate → HCID 14770844, compound

HRID 1090380Notes

Reaction equation

HRID 1090380 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[C:4]([F:15])[CH:3]=1.[BH4-].[Na+].[OH-].[Na+].C(OCC)(=O)C>C(O)C.C1COCC1>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)=[C:4]([F:15])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 14770833HCID 14770833, compound

Product 1

HCID 14770844HCID 14770844, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 15.0 g (54.5 mmol) of 3-(4-bromo-2,5-difluorophenyl) cyclopentanone in 150 ml of absolute ethanol and 10 ml of THF was added 2.5 g (65.4 mmol) of sodium borohydride portionwise. The reaction mixture was stirred for 21/2 hours at room temperature, then poured into a mixture of 250 ml of 1.0 N NaOH and 250 ml of ethyl acetate. The organic phase was washed with water, dried (MgSO4), and concentrated. The crude product was chromatographed over silica gel, eluting with 80:20 CHCl3 :EtOAc, to give 10.8 g (72%) of the desired product as a yellow oil.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed over silica gel
  5. washeluting with 80:20 CHCl3

Sources & evidence

ORD record
ord-32bd42ed5942492ab5d1a1ea27e5e11b
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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