Acetone → HCID 59216603, compound

HRID 2245295Notes

Reaction equation

HRID 2245295 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])([O-:3])=[O:2].[BH4-].[Na+].CC(C)=O.[NH4+].[Cl-]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][CH:14]([OH:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59216594HCID 59216594, compound

Product 1

HCID 59216603HCID 59216603, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(2,6-dinitrophenyl)-2-oxopropanoate (3.16 g, 11.2 mmol) is dissolved in dry methanol and cooled to 0° C. Sodium borohydride (0.13 g, 3.36 mmol) is added at 0° C. and stirring continued at 0° C. for 30 min. The mixture is warmed to room temperature and stirred for another 15 min. Acetone (10 ml) is added and subsequently of saturated aq. NH4Cl (5 ml) is added. The solvent is evaporated in vacuo, the remainder is dissolved in ethyl acetate and water, the organic layer is dried over magnesium sulfate, filtered and evaporated in vacuo. The crude product is purified with column chromatography on silica gel (eluent: cyclohexane/ethyl acetate, 1:1). Yield: 1.43 g (44%)

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. stirringstirred for another 15 min
  3. additionis added
  4. customThe solvent is evaporated in vacuo
  5. dissolutionthe remainder is dissolved in ethyl acetate
  6. dry with materialwater, the organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product is purified with column chromatography on silica gel (eluent: cyclohexane/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-2557ac45c1374bdea590576499d2f883
Source dataset
uspto-grants-2010_03
Patent number
US07683076B2

Reaction notes

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