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

HRID 844871노트

반응식

HRID 844871 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a4d1c794d7a845eb9e6cb2b2107b8bcb
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380387B1

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