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

HRID 571070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571070
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4f953ab4f82f482da4caa88d856b5261
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024032B2

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