Sodium hydride → HCID 67409937, compound

HRID 480689Notes

Reaction equation

HRID 480689 reaction equation
[H-].[Na+].[CH:3]([C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O.[Cl-].[NH4+]>O1CCCC1>[CH2:13]([O:12][C:10]([CH:9]=[CH:3][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22708243HCID 22708243, compound

Product 1

HCID 67409937HCID 67409937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% Sodium hydride (6.1 g, 0.15 mol) was dissolved in tetrahydrofuran. Subsequently, triethylphosphonoacetate (30.2 mL, 0.15 mol) was added dropwise under ice-cooling. After 30 minutes, tert-butyl 2-(3-formylphenoxy)-2-methylpropionate (33.6 g, 0.13 mol) was added under ice-cooling, the mixture was stirred for one hour. Thereafter, the temperature of the mixture was raised to room temperature, and the mixture was stirred for five hours. An aqueous ammonium chloride solution was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, followed by drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=9/1), whereby the target compound was obtained (39.1 g, 92%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for five hours
  4. extractionthe resultant mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialby drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=9/1), whereby the target compound
  7. customwas obtained (39.1 g, 92%)

Sources & evidence

ORD record
ord-69d9382a10ed44eeb5f5593b06a07fe5
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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