Ethyl Acetate → HCID 17995915, compound

HRID 58196

Reaction equation

HRID 58196 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[BH4-].[Na+].CCOC(C)=O>CO.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 27346124'-Fluoro-3'-nitroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 17995915HCID 17995915, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1-(4-fluoro-3-nitrophenyl)ethanone (1.0 g, 5.46 mmol) was dissolved in MeOH (15.0 ml) and stirred over ice bath. NaBH4 (0.62 g, 16.0 mmol) was added portionwise. Upon completion of the addition, the reaction mixture was stirred at rt for 10 minutes. The reaction mixture was poured into EtOAc and brine. The organic layer was separated, dried over MgSO4 and evaporated. The resulting material was purified by flash chromatography on silica eluting with 20% to 70% EtOAc/Hexane to afford the title compound (881 mg, yield: 87%). %). 1H-NMR (400 MHz, CDCl3) δ 1.53 (d, 4H) 4.99 (dd, 1H) 7.22-7.33 (m, 1H) 7.66 (ddd, 1H) 8.09 (dd, 1H)

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction mixture was stirred at rt for 10 minutes
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting material was purified by flash chromatography on silica eluting with 20% to 70% EtOAc/Hexane

Sources & evidence

ORD record
ord-95d290047f3d4487ba95a2a9bd813576
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

Loading…