Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diethyl benzylphosphonate | HCID 14122 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 22387817 | HCID 22387817 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22388154 | HCID 22388154 | 62.3% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06911469B2 |
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| Source dataset | uspto-grants-2005_06 |
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| ORD ID | ord-70577d39ad844d09a0471beb5f6ee8a9 |
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| Source note | uspto-grants-2005_06 |
|---|