Ethanol → HCID 21250279, compound

HRID 1953282Notes

Reaction equation

HRID 1953282 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].C(O)C.[BH4-].[Na+]>C(OCC)(=O)C>[CH:1]1([NH:12][C:11]2[CH:13]=[CH:14][C:8]([F:7])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8452CyclopentanoneHCID 677684-Fluoro-3-nitroanilineHCID 4311764Sodium borohydride

Product 1

HCID 21250279HCID 21250279, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6.7 g (0.08 mol) of cyclopentanone, 12.5 g (0.08 mol) of 4-fluoro-3-nitro-aniline and 30 ml titanium-IV-isopropoxide (0.1 mol) are stirred for 30 minutes at 40° C. and for one hour at ambient temperature. After the addition of 150 ml ethanol the reaction mixture is stirred for 30 minutes and then combined batchwise with 2.4 g (0.066 mol) of sodium borohydride. After 4 hours the reaction mixture is poured onto ice water and combined with ethyl acetate. After filtration the organic phase is separated off, dried and concentrated by evaporation. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (9:1). The desired fractions are combined and concentrated by evaporation.

Workup

  1. additionAfter 4 hours the reaction mixture is poured onto ice water
  2. filtrationAfter filtration the organic phase
  3. customis separated off
  4. customdried
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel
  7. washeluted with petroleum ether/ethyl acetate (9:1)
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7adadd891ffc48c093b5c15d9813db61
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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