Sodium hydride → HCID 68435388, Verbindung

HRID 1867382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867382
[OH:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[H-].[Na+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CN(C=O)C.C(Cl)Cl>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:1][C:2]2[C:3]([CH2:9][OH:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 1351283-Hydroxy-2-hydroxymethyl-6-methylpyridine

Produkt 1

HCID 68435388HCID 68435388, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.39 g (10 mmol) of the commercial 3-hydroxy-6-methyl-2-pyridinemethanol in 15 ml DMF was cooled (0° C.), treated with 0.52 g (13.00 mmol) of NaH (55% in oil) and after 30 min, with 1.35 mL (10.00 mmol) p-methoxybenzylchlorid. The suspension was stirred 1 h at 0° C. and 2 h at RT. The reaction mixture was diluted with CH2Cl2 and washed with 1M NaOH and brine. The organic layers were dried over magnesium sulfate, evaporated, purified by silica gel column (AcOEt) and crystallized (AcOEt/n-n-heptane) to give 1.55 g (60%) of the title compound as a white solid. MS: 260.0 (MH+).

Aufarbeitung

  1. washwashed with 1M NaOH and brine
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. customevaporated
  4. custompurified by silica gel column (AcOEt)
  5. customcrystallized (AcOEt/n-n-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-886c6b3c817f4e4caa1e757de466d6f9
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632829B2

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