N-methoxy-N,2-dimethylbenzamide → Cyclopropyl(2-methylphenyl)methanone

HRID 1349448ノート

反応式

HRID 1349448 の反応式
CON(C)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].[CH:14]1([Mg]Br)[CH2:16][CH2:15]1.O1CCCC1.C(OCC)(=O)C.Cl>O1CCCC1>[CH3:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([CH:14]1[CH2:16][CH2:15]1)=[O:12]

参加物

5

反応物 3

HCID 11344340N-methoxy-N,2-dimethylbenzamideHCID 21866389Hydrogen chloride-ethyl acetateHCID 178420628HCID 178420628、化合物

生成物 1

HCID 22382440Cyclopropyl(2-methylphenyl)methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-methoxy-2,N-dimethylbenzamide (3.55 g) obtained in Step 1 in tetrahydrofuran (40 ml) was added dropwise a solution of 1M cyclopropylmagnesium bromide-tetrahydrofuran (29.7 ml) under ice-cooling, and the mixture was stirred at room temperature for 12 hr. To the reaction mixture was added a 4N hydrogen chloride-ethyl acetate solution (10 ml), and the resulting mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed successively with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to give the title compound (1.05 g).

後処理

  1. temperaturecooling
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed successively with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

出典と根拠

ORDレコード
ord-70c93d3d9dfa4b019c7df781cabd0d43
出典データセット
uspto-grants-2007_05
特許番号
US07211685B2

反応ノート

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