Sodium hydride → HCID 66577269, compound

HRID 1528755Notes

Reaction equation

HRID 1528755 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:25][N:24]=[C:23]([CH3:26])[C:22]=2[CH:27]=O)=[CH:17][CH:16]=1>C1COCC1>[CH3:3][O:4][C:5](=[O:6])/[CH:7]=[CH:27]/[C:22]1[C:23]([CH3:26])=[N:24][O:25][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 821337925-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde

Product 1

HCID 66577269HCID 66577269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of sodium hydride (60% in mineral oil, 0.471 g, 11.03 mmol) in THF (10 mL) at 0° C. was added trimethyl phosphonoacetate (1.1 mL, 7.58 mmol). Additional THF (15 mL) was added to facilitate stirring and the solution was warmed to room temperature over 15 minutes. After cooling to 0° C., 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (1.834 g, 6.89 mmol) in THF (8 mL) was added and the reaction was stirred at room temperature for 10 minutes. The mixture was extracted with EtOAc and aqueous NH4Cl, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe reaction was stirred at room temperature for 10 minutes
  3. extractionThe mixture was extracted with EtOAc and aqueous NH4Cl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-476ddf98d02e4521a15ecce14450f7bd
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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