Dimethyl malonate → HCID 21265692, compound

HRID 566504Notes

Reaction equation

HRID 566504 reaction equation
[C:1]([O:8]C)(=O)[CH2:2][C:3]([O:5]C)=O.[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1.[NH4+].[Cl-]>CN(C=O)C.O>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:2]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)([CH2:1][OH:8])[CH2:3][OH:5])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromide

Product 1

HCID 21265692HCID 21265692, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To dimethyl malonate (6.60 g, 50 mmol) in DMF (100 mL) was added NaH (2.00 g, 50 mmol) and 4-bromomethyl bromobenzene (25 g, 100 mmol). After a period of 6 h at room temperature, 200 mL of saturated NH4Cl and 200 mL of H2O were added. The crude product was extracted with a mixture of toluene and ether, dried over Na2SO4, filtered and evaporated. To the oil dissolved in THF (300 mL) at 0° C. LAH (4.5 g) was added. After a period of 2 h at room temperature, the reaction was quenched with 20 mL of acetone and 300 mL of 20% potassium, sodium tartrate. The compound was extracted with EtOAc, dried over Na2SO4, evaporated and purified by flash chromatography to provide 19 g of material.

Workup

  1. extractionThe crude product was extracted with a mixture of toluene and ether
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionTo the oil dissolved in THF (300 mL) at 0° C
  6. additionLAH (4.5 g) was added
  7. waitAfter a period of 2 h at room temperature
  8. customthe reaction was quenched with 20 mL of acetone and 300 mL of 20% potassium, sodium tartrate
  9. extractionThe compound was extracted with EtOAc
  10. dry with materialdried over Na2SO4
  11. customevaporated
  12. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1a3bc97acc614191bd7e63ffffad2d9d
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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