Water → HCID 18429207, compound

HRID 1604164Notes

Reaction equation

HRID 1604164 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1)=[O:3].[BH4-].[Na+].O.C(OCC)(=O)C>C(O)C.C1COCC1>[N+:10]([C:8]1[CH:9]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:5]=[C:6]([N+:13]([O-:15])=[O:14])[CH:7]=1)([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2585693',5'-DinitroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 18429207HCID 18429207, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

3,5-Dinitroacetophenone (3.27 g, 0.0156 mol) was dissolved in a mixture of absolute ethanol (75 ml) and THF (37.5 ml) and the mixture was cooled to -10° C. NaBH4 (0.30 g, 7.9 mmol) was added and the mixture was stirred for 1 h at -10° C. Water (80 ml) and ethyl acetate were added, the phases were separated and the organic phase was washed with water (80 ml) and dried (Na2SO4). The solvents were removed by evaporation and the residue was purified by chromatography on neutral alumina using a mixture of pentane and ethyl acetate (1:1) as the eluent. Yield: 2.52 g (76%).

Workup

  1. customthe phases were separated
  2. washthe organic phase was washed with water (80 ml)
  3. dry with materialdried (Na2SO4)
  4. customThe solvents were removed by evaporation
  5. customthe residue was purified by chromatography on neutral alumina using
  6. additiona mixture of pentane and ethyl acetate (1:1) as the eluent

Sources & evidence

ORD record
ord-d4540085520543a7a6423af31a5f3800
Source dataset
uspto-grants-1999_11
Patent number
US05993780

Reaction notes

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