Water → Methyl 3-[(1,1-dimethylprop-2-yn-1-yl)oxy]benzoate

HRID 2190471ノート

反応式

HRID 2190471 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:13]([CH3:17])([CH3:16])[C:14]#[CH:15].N12CCCN=C1CCCCC2.O>C(#N)C.[Cu](Cl)Cl>[CH3:16][C:13]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])([CH3:17])[C:14]#[CH:15]

参加物

7

反応物 4

HCID 962WaterHCID 706791-Butyne, 3-chloro-3-methyl-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 88068Methyl 3-Hydroxybenzoate

生成物 1

HCID 76333229Methyl 3-[(1,1-dimethylprop-2-yn-1-yl)oxy]benzoate収率 28%

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of methyl 3-hydroxybenzoate (10.0 g, 65.7 mmol) in acetonitrile (200 mL) were added 3-chloro-3-methylbut-1-yne (20.0 g, 195 mmol) and copper (II) chloride (88 mg, 0.654 mmol) under ice-cooling, and the mixture was stirred for 15 min under ice-cooling. 1,8-Diazabicyclo[5.4.0]undec-7-ene (10 mL, 70.0 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water (300 mL), and the mixture was extracted with ethyl acetate (400 mL×2). The ethyl acetate layers were combined, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→0/100) to give the title compound (4.0 g, 28%) as a colorless oil.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturecooling
  4. stirringthe mixture was stirred at room temperature for 2 hr
  5. extractionthe mixture was extracted with ethyl acetate (400 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→0/100)

出典と根拠

ORDレコード
ord-986ffb9c5e014644beec986db52d2ec8
出典データセット
uspto-grants-2012_12
特許番号
US08324395B2

反応ノート

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