Water → HCID 86748241, Verbindung

HRID 2379530

Reaktionsgleichung

C([Li])CCC.[CH2:6]([O:13][CH2:14][O:15][CH2:16][Sn](CCCC)(CCCC)CCCC)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:30]/[C:31](/[CH2:35][CH2:36]/[CH:37]=[C:38](\[CH3:45])/[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])=[CH:32]\[CH2:33]Br.O>C1COCC1>[CH3:30]/[C:31](/[CH2:35][CH2:36]/[CH:37]=[C:38](\[CH3:45])/[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])=[CH:32]\[CH2:33][CH2:16][O:15][CH2:14][O:13][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

n-Butyl lithium (1.6M in hexane, 8.6 mL, 13.8 mmol) was added under nitrogen to a stirred solution of (benzyloxymethoxy)methyl-tri-(n-butyl) tin (6.1 g, 13.8 mmol) in THF (56 mL) at -78° C. The resulting mixture was stirred at -78° C. for 10 min, then added a solution of (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienylbromide (3.5 g, 12.3 mmol) in THF (4 mL) via a dropping funnel. The resulting mixture was stirred at -78° C. for 0.5 hours, then poured into cold water and extracted with ether. The ethereal extract was dried, filtered and evaporated to afford a residue, which was purified by flash chromatography on a silica gel column. Elution of the column with hexane:ether (25:1, v:v) provided the title compound as a colorless oil (2.39 g, 6.7 mmol, 54.5%).

Aufarbeitung

stirringThe resulting mixture was stirred at -78° C. for 0.5 hours
extractionextracted with ether
extractionThe ethereal extract
customwas dried
filtrationfiltered
customevaporated
customto afford a residue, which
customwas purified by flash chromatography on a silica gel column
washElution of the column with hexane:ether (25:1, v:v)

Quellen und Nachweise

ORD-Eintrag: ord-7ed07afb4d4b43f2ab4d18e4098f9c92
Quelldatensatz: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05362906

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