Benzyl Chloride → Ethyl 2-benzyl-1,3-dithiane-2-carboxylate

HRID 1379350

Reaktionsgleichung

[CH2:1]([O:3][C:4]([CH:6]1[S:11][CH2:10][CH2:9][CH2:8][S:7]1)=[O:5])[CH3:2].C([Li])CCC.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[CH2:17]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][CH2:8][CH2:9][CH2:10][S:11]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: -25 °C

Versuchsvorschrift

A solution of 3.0 g (15.6 mmol) of 2-ethoxycarbonyl-1,3-dithiane in 40 ml of dry tetrahydrofuran was cooled under inert atmosphere to -78° C. and treated with 7.5 ml (15.6 mmol) of n-butyllithium. The resulting solution was warmed to -25° C., stirred for 20 min, recooled to -78° C., treated with 1.8 ml (15.6 mmol) of benzyl chloride, and stirred at ambient temperature for 16 h. After quenching with aqueous ammonium chloride, the mixture was extracted with ether, washed sequentially with water, aqueous sodium thiosulfate, and brine, dried over MgSO4, and concentrated in vacuo. Flash chromatography using 5% ethyl acetate in hexane gave 3.9 g (88%) of the desired compound. 1H NMR (CDCl3) δ 1.33 (t, J=7 Hz, 3H), 1.85 (qt, J=14, 3 Hz, 1H), 2.11 (dm, J=14 Hz, 1H), 2.69 (dt, J=14, 4 Hz, 2 H), 3.23 (ddd, J=14, 12, 3 Hz, 2H), 3.38 (s, 2H), 4.27 (q, J=7 Hz, 2H), 7.25-7.35 (m, 5H). Mass spectrum (M+NH4)+ =300.

Aufarbeitung

customrecooled to -78° C.
stirringstirred at ambient temperature for 16 h
customAfter quenching with aqueous ammonium chloride
extractionthe mixture was extracted with ether
washwashed sequentially with water, aqueous sodium thiosulfate, and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-702a12b08c19450ea39ebd6aabd4e4d8
Quelldatensatz: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05670675

Verknüpfte Notizen

Wird geladen…