Sodium hydride → HCID 67396493, compound

HRID 1023711Notes

Reaction equation

HRID 1023711 reaction equation
C(OP([N:9]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)[C:10]([CH3:12])=[O:11])(OCC)=O)C.[H-].[Na+].[CH:25]([C:28]1[CH:29]=[C:30]([O:33][C:34]=1[CH:35]([CH3:37])[CH3:36])[CH:31]=O)([CH3:27])[CH3:26].[Cl-].[NH4+]>O1CCCC1>[CH:25]([C:28]1[CH:29]=[C:30]([CH:31]=[CH:12][C:10]([NH:9][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)=[O:11])[O:33][C:34]=1[CH:35]([CH3:37])[CH3:36])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 122588074,5-Bis(1-methylethyl)-2-furancarboxaldehydeHCID 67394042HCID 67394042, compound

Product 1

HCID 67396493HCID 67396493, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 4-[(diethoxyphosphoryl)acetamino]benzoate (165 mg, 0.501 mmol) in anhydrous tetrahydrofuran (3 ml) was cooled on an ice bath, and added with sodium hydride (60% mineral oil dispersion, 20 mg, 0.50 mmol) under an argon atmosphere, and the mixture was stirred for 5 minutes. The reaction mixture was added dropwise with a solution of 4,5-diisopropylfurfural (60 mg, 0.33 mmol) in anhydrous tetrahydrofuran (2 ml), and the mixture was further stirred at 0° C. for 50 minutes. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with chloroform. The reaction mixture was treated in a conventional manner, and then the resultant was purified by silica gel chromatography (2% methanol-chloroform) to obtain methyl 4-[[3-(4,5-diisopropyl-2-furanyl)acryloyl]amino]benzoate (115 mg, 97%) as colorless syrup-like substance.

Workup

  1. stirringthe mixture was further stirred at 0° C. for 50 minutes
  2. extractionthe mixture was extracted with chloroform
  3. additionThe reaction mixture was treated in a conventional manner
  4. customthe resultant was purified by silica gel chromatography (2% methanol-chloroform)

Sources & evidence

ORD record
ord-1767aaa3579b40f78e5724230643d698
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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