Sodium borohydride → 2-(2-Fluoro-4-nitrophenyl)-2-methylpropane-1,3-diol

HRID 1842964Notes

Reaction equation

HRID 1842964 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([CH3:20])([C:16](OC)=[O:17])[C:12](OC)=[O:13].[BH4-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([CH3:20])([CH2:16][OH:17])[CH2:12][OH:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70816610Dimethyl 2-(2-fluoro-4-nitrophenyl)-2-methylmalonate

Product 1

HCID 708166542-(2-Fluoro-4-nitrophenyl)-2-methylpropane-1,3-diolYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of dimethyl 2-(2-fluoro-4-nitrophenyl)-2-methylmalonate (1.0 g, 3.50 mmol, 1.0 eq) in methanol (20 mL) was added NaBH4 (0.67 gm, 17.63 mmol, 5.0 eq) at 0° C. and stirred at RT for 16 h. The mixture was diluted with water (20 mL), extracted with ethyl acetate (20 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, and the solvent was vaporated under reduced pressure. The crude product obtained was purified by CC using EtOAc/PE (2:3) to get 2-(2-fluoro-4-nitrophenyl)-2-methylpropane-1,3-diol (400 mg, 50%; TLC system: EtOAc/PE (1:1), Rf: 0.3).

Workup

  1. extractionextracted with ethyl acetate (20 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe crude product obtained
  5. customwas purified by CC

Sources & evidence

ORD record
ord-abac8a9f448042789d7896276bdf0167
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…