Water → Hex-5-yne 2-octylcycloprop-2-ene-1-carboxylate

HRID 840086노트

반응식

HRID 840086 반응식
[CH2:1]([C:9]1[CH:10]([C:12](Cl)=[O:13])[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[CH2:22]([OH:28])[CH2:23][CH2:24][CH2:25][C:26]#[CH:27].O>CCOCC>[CH2:1]([C:9]1[CH:10]([C:12]([OH:13])=[O:28])[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:27][CH2:26][CH2:25][CH2:24][C:23]#[CH:22]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 702345-Hexyn-1-olHCID 226216452-Octylcycloprop-2-ene-1-carbonyl chloride

생성물 1

HCID 86583675Hex-5-yne 2-octylcycloprop-2-ene-1-carboxylate수율 9.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of 2-octylcycloprop-2-ene-1-carbonyl chloride (330 mg, 1.5 mmol) in 5 ml of ether is added 1.5 ml of triethylamine. 5-Hexyn-1-ol (0.18 g, 1.8 mmol) was added to the reaction mixture, which was stirred at room temperature over the weekend. Water and additional ether were added, and the resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was washed with water and brine, dried over MgSO4, filtered and stripped. The product was chromatographed on silica gel to give 40 mg of 60% pure hex-5-yne 2-octylcycloprop-2-ene-1-carboxylate containing roughly 40% 2-octylcycloprop-2-ene-1-carboxylic acid.

후처리

  1. customthe resulting mixture was transferred to a separatory funnel
  2. customthe phases were separated
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe product was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-61a8b821db6646c68a7ed29ae31f866d
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365549B2

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