Dimethyl malonate → Dimethyl 2-(4-(diethoxymethyl)benzyl)malonate

HRID 566510Notes

Reaction equation

HRID 566510 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])=[CH:16][CH:15]=1>CN(C=O)C>[CH2:25]([O:24][CH:20]([O:21][CH2:22][CH3:23])[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:15][CH:16]=1)[CH3:26]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 6397611-(Bromomethyl)-4-(diethoxymethyl)benzene

Product 1

HCID 21265723Dimethyl 2-(4-(diethoxymethyl)benzyl)malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of dimethyl malonate (4.96 mL, 43 mmol) in DMF (80 mL) was added NaH (1.3 g 80% in mineral oil). After 20 min. a solution of 1-(bromomethyl)-4-(diethoxymethyl)benzene (2.37 g, 8.7 mmol) in DMF (5 mL) was added via double-tipped needle. After 1 h at 0° C., the reaction was quenched by the addition of saturated NH4Cl solution. The product was extracted with Et2O and the organic layer wash washed with H2O and brine. After drying (MgSO4) and filtration, the solvent was removed under vacuum. The crude was purified by flash chromatography (1:10 EtOAc/hexane) to yield a colorless oil (1:42 g).

Workup

  1. customthe reaction was quenched by the addition of saturated NH4Cl solution
  2. extractionThe product was extracted with Et2O
  3. washthe organic layer wash
  4. washwashed with H2O and brine
  5. customAfter drying
  6. filtration(MgSO4) and filtration
  7. customthe solvent was removed under vacuum
  8. customThe crude was purified by flash chromatography (1:10 EtOAc/hexane)
  9. customto yield a colorless oil (1:42 g)

Sources & evidence

ORD record
ord-7280c96838f74006b0a33739623be370
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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