Water → HCID 58136329, compound

HRID 1476070Notes

Reaction equation

HRID 1476070 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(OCC)=O)C.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29].O>C1COCC1>[F:19][C:20]1[CH:27]=[CH:26][C:23](/[CH:24]=[CH:11]/[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 58136329HCID 58136329, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 0.65 g of sodium hydride (60% in paraffin oil; 16.3 mmol) was initially charged in 25 ml of THF, and the mixture was cooled to 0° C. 4.29 g (17 mmol) of tert-butyl diethylphosphonoacetate were then slowly added dropwise. After 30 min of stirring, 2.5 g (14.8 mmol) of 4-fluoro-3-nitrobenzaldehyde were added. The reaction mixture was stirred at RT for 3 h, 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 on silica gel (mobile phase cyclohexane/ethyl acetate 50:1). This gave 3.37 g (85% of theory) of the target product.

Workup

  1. stirringThe reaction mixture was stirred at RT for 3 h
  2. extractionextracted three times with in each case 100 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-bea2df3409864bca883027495eead452
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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