Sodium hydride → Dibenzyl 2-{4-[(di-tert-butoxyphosphoryl)methyl]benzyl}malonate

HRID 566501Notes

Reaction equation

HRID 566501 reaction equation
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[H-].[Na+].Br[CH2:25][C:26]1[CH:44]=[CH:43][C:29]([CH2:30][P:31](=[O:42])([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][CH:27]=1>CN(C=O)C>[C:38]([O:37][P:31]([CH2:30][C:29]1[CH:43]=[CH:44][C:26]([CH2:25][CH:2]([C:1]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[CH:27][CH:28]=1)([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:42])([CH3:39])([CH3:40])[CH3:41]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 84754Dibenzyl malonateHCID 10915802Di(tert-butyl) [4-(bromomethyl)benzyl]phosphonate

Product 1

HCID 21265737Dibenzyl 2-{4-[(di-tert-butoxyphosphoryl)methyl]benzyl}malonateYield 19.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dibenzyl malonate (0.5 g) in DMF (8 mL), was added sequentially NaH (0.06 g, 80% in mineral oil), di(tert-butyl) [4-(bromomethyl)benzyl]phosphonate(0.66 g). The reaction mixture was stirred at room temperature for 1 h, then quenched with 20 mL of saturated aqueous NH4OAc solution and extracted with 50 mL EtOAc. The extract was dried over Na2SO4 and concentrated. The sesidue was purified by silica gel chromatography eluted with to give the title compound (0.2 g).

Workup

  1. customquenched with 20 mL of saturated aqueous NH4OAc solution
  2. extractionextracted with 50 mL EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe sesidue was purified by silica gel chromatography
  6. washeluted with

Sources & evidence

ORD record
ord-e108d89f32b94dd19a3d3fd22ebc4a9d
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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