Methyl iodide → Methyl 1-(p-tolyl)cyclopropanecarboxylate

HRID 2170618

반응식

HRID 2170618 반응식
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[CH2:14]1CCN2C(=NCCC2)CC1.CI>C(#N)C.CCOC(C)=O>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:14])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 986391-(p-Tolyl)cyclopropanecarboxylic acid

생성물 1

HCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylate수율 64%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(p-tolyl)cyclopropanecarboxylic acid (900 mg, 5.1 mmol) in acetonitrile (20 mL) was added DBU (917 μL) followed by methyl iodide (1.91 mL). The resulting solution was heated at reflux overnight, and then diluted with AcOEt. The mixture was washed with a 0.5 N HCl solution, a saturated solution of NaHCO3, and brine, dried on MgSO4, and concentrated. The resulting colorless oil was purified by chromatography on silica gel (Hexane/ethyl acetate 9/1) to afford the title compound as a colorless oil (622 mg, 64%).

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with a 0.5 N HCl solution
  4. dry with materiala saturated solution of NaHCO3, and brine, dried on MgSO4
  5. concentrationconcentrated
  6. customThe resulting colorless oil was purified by chromatography on silica gel (Hexane/ethyl acetate 9/1)

출처 및 근거

ORD 기록
ord-26cd73b39ef24724b7e91aee27671a72
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051265B2

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