Pyridine → prop-2-en-1-yl N-[4-(hydroxymethyl)phenyl]carbamate

HRID 910755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910755
[C:1](Cl)([O:3][CH2:4][CH:5]=[CH2:6])=[O:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1.N1C=CC=CC=1>ClCCl>[CH2:4]([O:3][C:1](=[O:2])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1)[CH:5]=[CH2:6]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 18052Allyl chloroformateHCID 693314-Aminobenzyl alcohol

Produkt 1

HCID 64795250prop-2-en-1-yl N-[4-(hydroxymethyl)phenyl]carbamateAusbeute 28,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Alloc-Cl (537 g) in dichloromethane (5 ml) was added dropwise to a solution of (4-amino-phenyl)-methanol (500 mg) and pyridine (5 ml) in dichloromethane (5 ml). After stirring for 2 h, the reaction mixture was diluted with dichloromethane and washed with water. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The title compound (243 mg) was obtained by recrystallization from dichloromethane. The mother liquor was chromatographed on silica gel in heptane/ethyl acetate=1/1 (v/v) as eluent which yielded another 245 mg of the title compound. Yield: 488 mg.

Aufarbeitung

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a59ebdd299764efdbc4ee62f373048d0
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022218B2

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