Methyl formate → Methyl 3-hydroxy-2-(1-methylpyrrol-2-yl)propenoate

HRID 256559

반응식

HRID 256559 반응식
[H-].[Na+].[CH3:3][N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH:14](OC)=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:15][CH:14]=[C:9]([C:5]1[N:4]([CH3:3])[CH:8]=[CH:7][CH:6]=1)[C:10]([O:12][CH3:13])=[O:11]

참가 물질

6

반응물 4

HCID 7865Methyl formateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 103992Methyl 1-methylpyrrol-2-acetate

생성물 1

HCID 67883841Methyl 3-hydroxy-2-(1-methylpyrrol-2-yl)propenoate수율 93.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (3.05 g, 50% dispersion in oil, 64 mmol) was washed with 40°-60° C. petroleum ether and then suspended in dry DMF (30 ml) under an atmosphere of nitrogen. A solution of methyl (1-methylpyrrol-2-yl)acetate (5 g, 32 mmol) and methyl formate (39.5 ml, 64 mmol) in DMF (10 ml) was then added dropwise at room temperature with vigorous stirring. After 3 hours, the reaction mixture was poured into 10% aqueous potassium carbonate (100 ml) and extracted with ether (2×100 ml). The aqueous layer was treated with concentrated hydrochloric acid and re-extracted with ether (2×100 ml). The combined ether layers were dried and evaporated to give methyl 3-hydroxy-2-(1-methylpyrrol-2-yl)propenoate (5.4 g) as an orange oil which was used without further purification.

후처리

  1. extractionextracted with ether (2×100 ml)
  2. additionThe aqueous layer was treated with concentrated hydrochloric acid
  3. extractionre-extracted with ether (2×100 ml)
  4. dry with materialThe combined ether layers were dried
  5. customevaporated

출처 및 근거

ORD 기록
ord-d6c00a01ede640e8902a1095fa4c51e6
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258360

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