Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Fluoro-3-nitrobenzaldehyde | HCID 598129 | — |
| Reactant | tert-Butyl diethylphosphonoacetate | HCID 2773685 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58136329 | HCID 58136329 | — |
Reaction Steps
Under argon, 0.65 g (16.3 mmol) of sodium hydride (as a 60% suspension in mineral oil) was initially charged in 25 ml of THF and cooled to 0° C. 4.29 g (17 mmol) of tert-butyl diethylphosphonoacetate were then slowly added dropwise. After 30 min, 2.5 g (14.8 mmol) of 4-fluoro-3-nitrobenzaldehyde were added. The reaction mixture was stirred at RT for 3 h and then poured into 100 ml of water and extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by flash chromatography (silica gel, mobile phase cyclohexane/ethyl acetate 50:1). This gave 3.37 g (85% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09018414B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-d0bd1f06d87d472db7052b73cf104b41 |
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| Source note | uspto-grants-2015_04 |
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