Water → HCID 13746901, 화합물

HRID 1732025

반응식

HRID 1732025 반응식
CO[C:3]([O:11]C)([O:9][CH3:10])[CH2:4][CH2:5][CH2:6][C:7]#[CH:8].C([Li])CCC.[CH2:18]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1.CCCCCC>[OH:28][CH:27]([C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]#[C:7][CH2:6][CH2:5][CH2:4][C:3]([O:9][CH3:10])=[O:11]

참가 물질

7

반응물 4

HCID 962WaterHCID 100129102-BenzylbenzaldehydeHCID 130965676,6,6-Trimethoxyhex-1-yneHCID 178418339Butyllithium

생성물 1

HCID 13746901HCID 13746901, 화합물수율 56%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a stirred mixture of 2.19 g (12.73 mmol) 1,1,1-trimethoxy-5-hexyne in 15 ml dry tetrahydrofuran (THF) at -78° under nitrogen was added 8.37 ml of 1.52M n-butyllithium (12.73 mmol) in hexane dropwise. The mixture was stirred at -78° for 1 hour and 2.0 g of 2-benzylbenzaldehyde (10.20 mmol) in 10 ml dry THF was added dropwise at -78°. The mixture was stirred at room temperature for 12 hours and poured into water. The reaction mixture was extracted with ether (2×75 ml) and the combined organic layers were washed with water (50 ml), saturated sodium chloride (50 ml), and dried (MgSO4). Filtration and evaporation left an oil that was purified by flash chromatography to give the title compound in 56% yield (2.02 g). NMR (CDCl3, 200 MHz) δ: 1.80 (m, 2H), 2.25-2.50 (m, 5H), 3.67 (s, 3H), 4.18 (br s, 2H), 5.60 (s, 1H), 7.12-7.75 (m, 9H). Mass spectrum: m/z=322 (M+).

후처리

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. extractionThe reaction mixture was extracted with ether (2×75 ml)
  3. washthe combined organic layers were washed with water (50 ml), saturated sodium chloride (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation
  6. waitleft an oil that
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-13e82e3a0ed34d6a81e2bcd79eb8fcbe
출처 데이터셋
uspto-grants-1986_11
특허 번호
US04624964

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