Dimethyl 2-methyl-2-(4-nitrophenyl)malonate → 2-Methyl-2-(4-nitrophenyl)-1,3-propanediol

HRID 1842970Notes

Reaction equation

HRID 1842970 reaction equation
[CH3:1][C:2]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)([C:7](OC)=[O:8])[C:3](OC)=[O:4].[BH4-].[Na+]>CO>[CH3:1][C:2]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)([CH2:3][OH:4])[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 1485451Dimethyl 2-methyl-2-(4-nitrophenyl)malonateHCID 4311764Sodium borohydride

Product 1

HCID 136636512-Methyl-2-(4-nitrophenyl)-1,3-propanediolYield 40.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of dimethyl 2-methyl-2-(4-nitrophenyl)malonate (5 g, 18.72 mmol, 1.0 eq) in methanol (50 mL) was added NaBH4 (2.12 g, 56.17 mmol, 3.0 eq) at 0° C. and stirred at RT for 16 h. The solvent was evaporated and the residue was diluted with water (50 mL). The product was extracted with EtOAc (2×60 mL). The combined organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4, evaporated under reduced pressure. The crude product obtained was purified by CC using EtOAc/PE (1:1) to get 2-methyl-2-(4-nitrophenyl)propane-1,3-diol (1.6 g 40%; TLC system: EtOAc/PE (1:1), Rf: 0.2).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water (50 mL)
  3. extractionThe product was extracted with EtOAc (2×60 mL)
  4. washThe combined organic layer was washed with brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude product obtained
  8. customwas purified by CC

Sources & evidence

ORD record
ord-3f06fc4ffeee4068978defcfc0590807
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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