Hydrochloric Acid → 4-Formyl-3-methylisoxazole-5-carboxylic acid

HRID 1591000노트

반응식

HRID 1591000 반응식
C([Li])CCC.[C:6]([NH-:10])([CH3:9])([CH3:8])[CH3:7].[CH3:11][C:12]1[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[O:14][N:13]=1.Cl.[O:21]1CCC[CH2:22]1>O.CN(C)C=O>[C:6]([NH-:10])([CH3:9])([CH3:8])[CH3:7].[CH:22]([C:16]1[C:12]([CH3:11])=[N:13][O:14][C:15]=1[C:17]([OH:19])=[O:18])=[O:21]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8530853-Methylisoxazole-5-carboxylic acidHCID 20624633t-ButylamideHCID 178418339Butyllithium

생성물 2

HCID 197652694-Formyl-3-methylisoxazole-5-carboxylic acidHCID 20624633t-Butylamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

56 ml of butyllithium (1.6 molar solution in n-hexane) are added dropwise, at -78° C., to 8 g of the tertbutylamide of 3-methylisoxazole-5-carboxylic acid in 150 ml of tetrahydrofuran. The mixture is stirred for 1 hour, after which 22 ml of dimethylformamide are slowly added dropwise. The mixture is allowed to reach room temperature overnight and is hydrolyzed with water, neutralized with concentrated hydrochloric acid and extracted with ether. The oil which remains after evaporation is chromatographed over silica gel sing cyclohexane/ethyl acetate. The tert-butylamide of 4-formyl-3-methylisoxazole-5-carboxylic acid is obtained as the first fraction, in the form of pale yellow crystals of melting point 36°-38° C. (compound No. 2).

후처리

  1. waitto reach room temperature overnight
  2. extractionextracted with ether
  3. customafter evaporation
  4. customis chromatographed over silica gel

출처 및 근거

ORD 기록
ord-3ebaa3a36ff3419fbf3c2a9676d62a7e
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05205854

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