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

HRID 467504노트

반응식

HRID 467504 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 72407279tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate수율 82.1%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매2회HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eeac880c6cbc41239d21c5dd6bdfa932
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623869B2

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