Diethyl Malonate → HCID 69590757, compound

HRID 857227Notes

Reaction equation

HRID 857227 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].[CH3:14][C:15]1[O:19][C:18]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH2:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br>O1CCCC1.CN(C)C=O>[CH3:14][C:15]1[O:19][C:18]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)=[N:17][C:16]=1[CH2:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][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 21866742HCID 21866742, compound

Product 1

HCID 69590757HCID 69590757, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 15 ml of dry tetrahydrofuran and 7 ml of dry N,N-dimethylformamide, 0.88 g of 60% sodium hydride was added. To the mixture was added dropwise 4.40 g of diethyl malonate with stirring under ice-cooling. After 15-minute-stirring, a solution of 3.93 g of 3-{[5-methyl-2-(p-tolyl)oxazol-4-yl]methyl}benzyl bromide/5 ml of dry tetrahydrofuran was added and stirred for 1 hour under ice-cooling. The reaction solution was poured into ice-cold water, extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=5:1) to provide 3.95 g of the objective compound as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringAfter 15-minute-stirring
  3. stirringstirred for 1 hour under ice-
  4. temperaturecooling
  5. additionThe reaction solution was poured into ice-cold water
  6. extractionextracted with ethyl acetate
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=5:1)

Sources & evidence

ORD record
ord-bf43c778d03f452bbe745605bf10a41c
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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