Water → HCID 13746901, Verbindung

HRID 1732025

Reaktionsgleichung

Reaktionsgleichung von HRID 1732025
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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 13746901HCID 13746901, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-13e82e3a0ed34d6a81e2bcd79eb8fcbe
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04624964

Verknüpfte Notizen

Wird geladen…