Ethyl formate → HCID 68647944, compound

HRID 1161760Notes

Reaction equation

HRID 1161760 reaction equation
OC=[C:3]([C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=CN=1)=[O:5].[N:19]1C=CC=C[C:20]=1NC(=O)CC1ON=C(C)C=1.[H-].[Na+].C(OCC)=O>C1COCC1.[OH-].[Na+]>[N:19]1[CH:10]=[CH:11][CH:12]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][C:13]2[O:17][N:16]=[C:15]([CH3:18])[CH:14]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 68648365HCID 68648365, compoundHCID 136380314HCID 136380314, compound

Product 1

HCID 68647944HCID 68647944, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

General method for the synthesis of α-hydroxymethylene-3-methyl-N-pyridyl-5-isoxazoleacetamide: A solution of N-pyridyl-3-methyl-5-isoxazoleacetamide (1.1 g, 5 mmol) in THF (20 mL) was slowly added to a suspension of NaH (60% in oil; 0.5 g, 12.5 mmol) in 10 mL of THF. The reaction mixture was stirred at rt for 30 mins. and then ethyl formate (2 mL, 25 mmol) was added. After stirring at rt overnight, the reaction was conc. in vacuo and the residue was dissolved in 100 mL of a 1N aqueous NaOH solution and extracted with 25 mL of EtOAc. The aqueous layer was separated and brought to pH 5-6 with the addition of an aqueous 6N HCl solution. The resulting light yellow precipitate was collected and washed with cold water, affording the desired product.

Workup

  1. stirringAfter stirring at rt overnight
  2. extractionextracted with 25 mL of EtOAc
  3. customThe aqueous layer was separated
  4. additionbrought to pH 5-6 with the addition of an aqueous 6N HCl solution
  5. customThe resulting light yellow precipitate was collected
  6. washwashed with cold water

Sources & evidence

ORD record
ord-4ba71bbe3acf46d88180b3103bdcbf0c
Source dataset
uspto-grants-2010_10
Patent number
US07820663B2

Reaction notes

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