Sodium hydride → Dimethyl 2-(4-bromobenzyl)-2-[4-(diethoxymethyl)benzyl]malonate

HRID 566507Notes

Reaction equation

HRID 566507 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH:7]([C:12]([O:14][CH3:15])=[O:13])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[CH:22][CH:21]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([CH:26]([O:27][CH2:28][CH3:29])[O:30][CH2:31][CH3:32])=[CH:24][CH:25]=2)([C:8]([O:10][CH3:11])=[O:9])[C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6397611-(Bromomethyl)-4-(diethoxymethyl)benzeneHCID 2801290Dimethyl 2-(4-bromobenzyl)malonate

Product 1

HCID 21265763Dimethyl 2-(4-bromobenzyl)-2-[4-(diethoxymethyl)benzyl]malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of dimethyl 2-(4-bromobenzyl)malonate (4.2 g), 1-(bromomethyl)-4-(diethoxymethyl)benzene (4 g) in DMF (50 mL) was treated with NaH (0.8 g, 60% in mineral oil). The mixture was stirred for 2 h at 60° C., and then quenched with 100 mL of 50% saturated NH4Cl. The product was extracted with 200 mL of 2:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated, and dried under vacuum to give the title compound which was used without further purification.

Workup

  1. customquenched with 100 mL of 50% saturated NH4Cl
  2. extractionThe product was extracted with 200 mL of 2:1 hexane/EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-93c21e67cde848aeb8e9cc9c91906482
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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