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

HRID 1504218ノート

反応式

HRID 1504218 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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-hydrochloric 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.

後処理

  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-hydrochloric 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

出典と根拠

ORDレコード
ord-8de52dce24724b98bce96a203f04e86d
出典データセット
uspto-grants-2015_12
特許番号
US09212187B2

反応ノート

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