Sodium hydride → HCID 89120268, compound

HRID 591271Notes

Reaction equation

HRID 591271 reaction equation
[H-].[Na+].[CH3:3][C:4]([O:7][C:8]([CH2:10][P:11]([O:15][CH3:16])([O:13][CH3:14])=[O:12])=[O:9])([CH3:6])[CH3:5].[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH:10]([P:11]([O:15][CH3:16])([O:13][CH3:14])=[O:12])[C:8]([O:7][C:4]([CH3:3])([CH3:5])[CH3:6])=[O:9])=[CH:31][CH:32]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 104927561-(Benzyloxy)-4-(bromomethyl)benzene

Product 1

HCID 89120268HCID 89120268, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 1.71 g sodium hydride (50% in oil, 35.7 mmol) in anhydrous tetrahydrofuran (100 mL) was added a solution of 8.0 g tert-butyl P,P-dimethylphosphonoacetate (35.7 mmol) in anhydrous tetrahydrofuran (25 mL) at room temperature, and the resulting mixture was stirred for 1 h at room temperature. Subsequently, a solution of 4.95 g 4-benzyloxybenzyl bromide (17.8 mmol; prepared according to Helv. Chim. Acta, 2002, 85, 3422) in tetrahydrofuran (25 mL) was added, and the mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride (50 mL) was then added, the mixture was stirred for another 20 minutes at room temperature, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated. Column chromatography over silica gel (2.5→50% ethyl acetate in hexane) gave 1.48 g (20% yield based on 4-benzyloxybenzyl bromide) of the target compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. stirringthe mixture was stirred for another 20 minutes at room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customColumn chromatography over silica gel (2.5→50% ethyl acetate in hexane) gave 1.48 g (20% yield based on 4-benzyloxybenzyl bromide) of the target compound

Sources & evidence

ORD record
ord-d6df63d8cfe04b60ab7198e3baf87ef6
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

Loading…