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

HRID 2170618

反応式

HRID 2170618 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylate収率 64%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-26cd73b39ef24724b7e91aee27671a72
出典データセット
uspto-grants-2015_06
特許番号
US09051265B2

関連ノート

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