Water → 1-(3-bromophenyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one

HRID 571070노트

반응식

HRID 571070 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[C:12]([OH:14])[C:11](=[O:15])[CH:10]=[C:9]2[CH2:16][OH:17])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Cl)=[CH:28][CH:27]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[C:12]([O:14][CH2:32][C:29]3[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=3)[C:11](=[O:15])[CH:10]=[C:9]2[CH2:16][OH:17])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 674085331-(3-bromophenyl)-5-hydroxy-2-(hydroxymethyl)pyridin-4(1H)-one

생성물 1

HCID 674179621-(3-bromophenyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a mixture of 1-(3-bromo-phenyl)-5-hydroxy-2-hydroxymethyl-1H-pyridin-4-one and K2CO3 (5.17 g, 37.5 mmol) in 50 mL of DMF was added 2.35 g of PMBCl (15 mmol) dropwise, and the reaction mixture was stirred at 80° C. for 3 h. After cooling to room temperature, the mixture was poured into 200 mL of water and extracted with EtOAc (50 mL) three times. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. Most of the volatiles were removed in vacuo and the resulting solid was collected and washed with EtOAc to obtain 1-(3-bromophenyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one. 1H NMR (400 MHz, DMSO-d6): δ 7.75 (d, J=8.0 Hz, 2H), 7.49 (d, J=4.0 Hz, 2H), 7.46 (s, 1H), 7.31 (d, J=7.6 Hz, 2H), 6.92 (d, J=7.6 Hz, 2H), 6.32 (s, 1H), 5.46 (s, 1H), 4.86 (s, 2H), 3.74 (s, 3H). ESI (M+H)+ 415.9/417.9

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (50 mL) three times
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customMost of the volatiles were removed in vacuo
  6. customthe resulting solid was collected
  7. washwashed with EtOAc

출처 및 근거

ORD 기록
ord-4f953ab4f82f482da4caa88d856b5261
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024032B2

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