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

HRID 895877노트

반응식

HRID 895877 반응식
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]

참가 물질

5

반응물 3

HCID 11344340N-methoxy-N,2-dimethylbenzamideHCID 21866389Hydrogen chloride-ethyl acetateHCID 178420628HCID 178420628, 화합물

생성물 1

HCID 22382440Cyclopropyl(2-methylphenyl)methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-687ae10eaff540b09a1259bda97bc81b
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916956B2

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