Sodium hydride → HCID 15480691, compound

HRID 2422261Notes

Reaction equation

HRID 2422261 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:19]([O:26][C:27]1[CH:28]=[CH:29][C:30](/[CH:31]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:33][CH:34]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 15480691HCID 15480691, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution (100 mL) of tert-butyl diethylphosphonoacetate (13.8 g, 51.8 mmol) in tetrahydrofuran was added 60% sodium hydride (2.45 g, 61.2 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 15 min. Then, to this mixture was added dropwise a solution (138 mL) of 4-(benzyloxy)benzaldehyde (10 g, 47.1 mmol) in tetrahydrofuran with stirring at 0° C., and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, and washed with 5% aqueous potassium hydrogensulfate solution and saturated brine. The ethyl acetate layer was dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (13.7 g, yield 94%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 15 min
  2. stirringwith stirring at 0° C.
  3. stirringthe mixture was stirred at room temperature for 3 hrs
  4. concentrationThe reaction mixture was concentrated
  5. additionthe residue was diluted with ethyl acetate
  6. washwashed with 5% aqueous potassium hydrogensulfate solution and saturated brine
  7. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d8109be69634c0f839a659ce82d5a71
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

Loading…