Water → HCID 13746901、化合物

HRID 1732025

反応式

HRID 1732025 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 13746901HCID 13746901、化合物収率 56%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-13e82e3a0ed34d6a81e2bcd79eb8fcbe
出典データセット
uspto-grants-1986_11
特許番号
US04624964

関連ノート

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