tert-butyl N-[4-(hydroxymethyl)-2-methylphenyl]carbamate → 4-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-methylbenzaldehyde

HRID 844871ノート

反応式

HRID 844871 の反応式
[CH3:1][C:2]([CH3:17])([O:4][C:5]([NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[CH3:16])=[O:6])[CH3:3]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:3][C:2]([CH3:17])([O:4][C:5]([NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][C:9]=1[CH3:16])=[O:6])[CH3:1]

参加物

4

反応物 1

HCID 22981315tert-butyl N-[4-(hydroxymethyl)-2-methylphenyl]carbamate

生成物 1

HCID 226137184-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-methylbenzaldehyde収率 77.5%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-[(1,1-dimethylethoxy)carbonyl]amino-3-methylbenzyl alcohol (42.9 mmol, 10.18 g) in dichloromethane (85 mL) was added manganese dioxide (138 mmol, 12 g) and 4A molecular sieves (6 g) at room temperature. The reaction mixture was stirred for 76 h at room temperature and was filtered through a pad of celite washing with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography using a Biotage (40m) column to obtain 7.82 g (77% yield) of 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methylbenzaldehyde as a white solid: mp 109-111° C. EI-HRMS m/e calcd for C13H17NO3 (M+) 235.1208, found 235.1207.

後処理

  1. filtrationwas filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-a4d1c794d7a845eb9e6cb2b2107b8bcb
出典データセット
uspto-grants-2002_04
特許番号
US06380387B1

反応ノート

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