Water → 5-(2,2-Dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one

HRID 69047노트

반응식

HRID 69047 반응식
[H-].[Na+].[CH3:3][C:4]1[O:12][C:11]2[CH:10]=[CH:9][NH:8][C:7](=[O:13])[C:6]=2[CH:5]=1.C[O:15][CH:16]([O:19]C)[CH2:17]Br.O>CN(C=O)C>[OH:15][CH:16]([OH:19])[CH2:17][N:8]1[CH:9]=[CH:10][C:11]2[O:12][C:4]([CH3:3])=[CH:5][C:6]=2[C:7]1=[O:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 153662842-methylfuro[3,2-c]pyridin-4(5H)-one

생성물 1

HCID 669600005-(2,2-Dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (60% in oil, 0.32 g) was suspended in DMF (10 ml), and was cooled to 0° C. in an ice water bath. 2-Methyl-5H-furo[3,2-c]pyridin-4-one (0.57 g) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. Bromoacetaldehyde dimethylacetal (2.3 ml) was added thereto, and the mixture was stirred at 80° C. for 5 hours. Water was added to the reaction liquid, followed by extraction by ethyl acetate. The organic layer was dried over sodium sulfate, and condensed under reduced pressure. A 3N-hydrochrolic acid (2 ml) was added to an acetone solution (10 ml) of the residue, and the liquid was stirred at 70° C. for 10 hours. Water was added to the reaction liquid and stirred at room temperature. The precipitated insoluble matter was separated, washed with water, and dried to give the title compound (0.56 g) as a white solid.

후처리

  1. stirringthe mixture was stirred at 80° C. for 5 hours
  2. extractionfollowed by extraction by ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
  4. additionA 3N-hydrochrolic acid (2 ml) was added to an acetone solution (10 ml) of the residue
  5. stirringthe liquid was stirred at 70° C. for 10 hours
  6. additionWater was added to the reaction liquid
  7. stirringstirred at room temperature
  8. customThe precipitated insoluble matter was separated
  9. washwashed with water
  10. customdried

출처 및 근거

ORD 기록
ord-5474c7f342d74955a8aa79eac90921e7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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