Diethyl Malonate → Diethyl (3-bromobenzyl)malonate

HRID 1796361Notes

Reaction equation

HRID 1796361 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br>O1CCCC1.CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromide

Product 1

HCID 11056569Diethyl (3-bromobenzyl)malonate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60%, 1.6 g) was suspended into 20 ml of dry tetrahydrofuran/15 ml of dry N,N-dimethyl formamide, and 7.6 ml of diethyl malonate was added dropwise under ice-cooling. The mixture was stirred for 15 minutes. A solution of 5 g of 3-bromobenzyl bromide/10 ml of dry tetrahydrofuran was then added, and stirred for 1 hour under ice-cooling. To the reaction solution was added ice-cold water, and extracted with ether, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=10:1) to provide 5.41 g of the objective compound as colorless oil.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. stirringstirred for 1 hour under ice-
  4. temperaturecooling
  5. additionTo the reaction solution was added ice-cold water
  6. extractionextracted with ether
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-853c9ae8939149e3b416f630a62aa842
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Reaction notes

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