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

HRID 467504ノート

反応式

HRID 467504 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒2 回HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eeac880c6cbc41239d21c5dd6bdfa932
出典データセット
uspto-grants-2014_01
特許番号
US08623869B2

反応ノート

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