Water → (3-Methyloxetan-3-yl)methyl hex-5-ynoate

HRID 432883ノート

反応式

HRID 432883 の反応式
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[CH3:9][C:10]1([CH2:14]O)[CH2:13][O:12][CH2:11]1.Cl.C(N=C=NCCCN(C)C)C.O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:9][C:10]1([CH2:14][O:7][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6])[CH2:13][O:12][CH2:11]1

参加物

7

反応物 4

HCID 962WaterHCID 1378373-Methyl-3-oxetanemethanolHCID 1430365-Hexynoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 13123201(3-Methyloxetan-3-yl)methyl hex-5-ynoate収率 95.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-hexynoic acid (10.0 g) and 3-methyl-3-oxetane methanol (10.0 g) in methylene chloride (50 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (20.5 g), and 4-dimethylaminopyridine (1.09 g) were added under cooling with ice. The mixture was stirred at room temperature for 45 minutes. The reaction mixture was poured into iced water and extracted with ethyl acetate. The organic layer was washed by water and an aqueous saturated solution of sodium chloride, sucessively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified with silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the title compound (16.7 g) having the following physical data.

後処理

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed by water
  4. dry with materialan aqueous saturated solution of sodium chloride, sucessively, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-0b9397df769947b8a8b4e5c84888012e
出典データセット
uspto-grants-2003_12
特許番号
US06664281B1

反応ノート

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