Ethyl Acetate → HCID 21474795, compound

HRID 2294365Notes

Reaction equation

HRID 2294365 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([C:13]([CH3:26])([CH3:25])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH2:8]1.C(OCC)(=O)C.[BH4-].[Na+]>C(O)(C)(C)C>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:13]([N:9]2[CH2:8][CH:7]([CH2:6][O:5][C:4]3[CH:27]=[CH:28][CH:29]=[C:2]([Cl:1])[CH:3]=3)[O:11][C:10]2=[O:12])([CH3:25])[CH3:26])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 21474804HCID 21474804, compound

Product 1

HCID 21474795HCID 21474795, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

6.32 g of stannous chloride dihydrate were added to a solution of 2.34 g of 5-(3-chlorophenoxymethyl)-3-[2-(4-nitrophenoxy)-1,1-dimethylethyl]oxazolidin-2-one (prepared as described in Preparation 108) in 70 ml of a 9:1 by volume mixture of ethyl acetate and t-butanol. 0.11 g of sodium borohydride was then added to the mixture over an oil bath at 66° C. The mixture was stirred at the same temperature for 6 hours. At the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure, and the residue was neutralized by adding an aqueous sodium hydrogencarbonate solution. The insolubles which had precipitated were removed by filtration, and the filtrate was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extract by evaporation under reduced pressure, to give 1.96 g of the title compound having an Rf value of 0.34 (on silica gel thin layer chromatography, using a 4:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customAt the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure
  2. additionby adding an aqueous sodium hydrogencarbonate solution
  3. customThe insolubles which had precipitated
  4. customwere removed by filtration
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe extract was washed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe ethyl acetate was removed from the
  9. extractionextract by evaporation under reduced pressure

Sources & evidence

ORD record
ord-67c27e236aa74ba7a1a6f3adaab5dc5d
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

Loading…