Water → HCID 22388154, compound

HRID 1072890Notes

Reaction equation

HRID 1072890 reaction equation
[H-].[Na+].[Si:3]([O:10][CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[Cl:20])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:21](P(=O)(OCC)OCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[Si:3]([O:10][CH2:11][C:12]1[CH:19]=[CH:18][C:15](/[CH:16]=[CH:21]/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:14][C:13]=1[Cl:20])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 22387817HCID 22387817, compound

Product 1

HCID 22388154HCID 22388154, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Sodium hydride (70% in mineral oil, 81 mg) was added to a mixture of 4-((tert-butyldimethylsilyloxy)methyl)-3-chlorobenzaldehyde (571 mg) and diethyl benzylphosphonate (502 mg) in N,N-dimethylformamide (2 ml) under a nitrogen atmosphere at room temperature and the mixture was stirred at 40° C. for 2 hr. Water was added to the reaction mixture and the resulting product was extracted three times with ether. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=50/1) to give the objective compound (448 mg) as a colorless oil.

Workup

  1. extractionthe resulting product was extracted three times with ether
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-70577d39ad844d09a0471beb5f6ee8a9
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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