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

HRID 432883노트

반응식

HRID 432883 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0b9397df769947b8a8b4e5c84888012e
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664281B1

반응 노트

불러오는 중…