Water → HCID 58136329, compound

HRID 1476053Notes

Reaction equation

HRID 1476053 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 (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.

Workup

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

Sources & evidence

ORD record
ord-d0bd1f06d87d472db7052b73cf104b41
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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