tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate → tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate

HRID 467504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467504
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Komponenten

4

Edukt 1

HCID 58070261tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate

Produkt 1

HCID 72407279tert-butyl N-[1-(3-formylphenyl)ethyl]carbamateAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate (4.91 g, 19.54 mmol) in DCM (40 mL) was added MnO2 (13.59 g, 156.3 mmol) and the reaction mixture was stirred at ambient temperature for 48 hours. An additional portion of MnO2 (3 g 34.5 mmol) was added and the reaction mixture was stirred at ambient temperature for an additional 12 hours. The reaction mixture was filtered through a pad of Celite and the filtrate concentrated in vacuo to give the sub-title compound as a colourless oil (4.0 g, 82% Yield). 1H NMR (400 MHz, DMSO) δ 1.30-1.41 (m, 12H) 4.64-4.75 (m, 1H), 7.55 (dd, 2H), 7.64 (d, 1H), 7.78 (d, 1H), 7.83 (s, 1H) and 10.00 (s, 1H) ppm; MS (ES+) 250.5.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at ambient temperature for an additional 12 hours
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eeac880c6cbc41239d21c5dd6bdfa932
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623869B2

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