N-Methoxy-N-methyl-2-(2-methylphenyl)acetamide → 1-(2-Methylphenyl)propan-2-one

HRID 706381ノート

反応式

HRID 706381 の反応式
[CH3:1][Mg]Cl.CON(C)[C:7](=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15]>C1COCC1>[C:10]1([CH3:15])[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][C:7](=[O:16])[CH3:1]

参加物

4

反応物 2

HCID 21099310N-Methoxy-N-methyl-2-(2-methylphenyl)acetamideHCID 178418332HCID 178418332、化合物

生成物 1

HCID 27341091-(2-Methylphenyl)propan-2-one収率 81.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
47.5 °C

実験手順

A solution of CeCl3 (114.4 g, 0.45 mol) in THF (4 L) was degassed for 1 h and heated to 45-50° C. for 5 h. When the solution was cooled to −10˜−5° C., MeMgCl (193.2 g, 2.6 mol) in THF was added and the mixture was stirred for 1 h at −10˜−5° C. After amide 34 (256 g, 1.3 mol) was charged into the reaction mixture at −10˜−5° C., the mixture was stirred for 5 h at 10-20° C. After the reaction was complete monitored by LCMS, the mixture was quenched by 1M HCl, and then partitioned with water and EtOAc. The organic phase was dried over Na2SO4 and concentrated. The crude residual was further purified by flash chromatography on silica gel (2-10% EtOAc/PE) to give 35 (157 g, 80% yield). 1H NMR (CDCl3, 400 MHz): δ 7.1-6.91 (d, 4H), 3.55 (s, 3H), 2.25 (s, 3H), 2.05 (s, 3H); MS (ESI) m/e [M+H]+: 149.05.

後処理

  1. temperatureWhen the solution was cooled to −10˜−5° C.
  2. stirringthe mixture was stirred for 5 h at 10-20° C
  3. customthe mixture was quenched by 1M HCl
  4. custompartitioned with water and EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude residual was further purified by flash chromatography on silica gel (2-10% EtOAc/PE)

出典と根拠

ORDレコード
ord-f9763f3807e246008052abc54f36420c
出典データセット
uspto-grants-2015_11
特許番号
US09174989B2

反応ノート

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