Boron tribromide → 5-(2-Butyl-1,3-dithiolan-2-yl)benzene-1,3-diol

HRID 1376245

Reaktionsgleichung

B(Br)(Br)Br.[CH2:5]([C:9]1([C:14]2[CH:19]=[C:18]([O:20]C)[CH:17]=[C:16]([O:22]C)[CH:15]=2)[S:13][CH2:12][CH2:11][S:10]1)[CH2:6][CH2:7][CH3:8]>C(Cl)Cl>[CH2:5]([C:9]1([C:14]2[CH:15]=[C:16]([OH:22])[CH:17]=[C:18]([OH:20])[CH:19]=2)[S:10][CH2:11][CH2:12][S:13]1)[CH2:6][CH2:7][CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Boron tribromide (32.9 ml of 1M soln, 32.9 mmol) was added to a solution of Compound 9 (4.51 g, 3.23 mmol) in CH2Cl2 (546 ml) under argon at −78° C. The reaction temperature was then raised slowly to 0° C. over a period of 3 hrs. Stirring was continued at 0° C. for 12–14 hrs or until completion of reaction. Unreacted boron tribromide was destroyed by adding methanol, solvent removed and the residual oil diluted with diethyl ether. The organic phase was washed with saturated NaHCO3, water and brine, dried and concentrated. The residue was resolved over silica gel eluting with diethylether/hexanes (4:6) to yield 0.675 g (74.1%) of Compound 16 as a waxy solid. Rf=0.28 (hexane:ethyl acetate 8:2) 1H NMR δ 6.79 (d, J=2.5 Hz, 2H), 6.23 (t, J=2H, 1H), 5.30 (br s, 2H), 3.38–3.19 (m, 4H), 2.25 (t, J=9.75 Hz, 2H), 1.29–1.18 (m, 4H), 0.83 (t, J=7 Hz, 3H); 13C NMR δ 156.24, 148.45, 107.23, 101.50, 73.90, 45.50, 39.01, 29.96, 22.74, 13.86; MS: (ESI, Neg.) m/z 269 ([M−H]−).

Aufarbeitung

customwas continued at 0° C. for 12–14 hrs or until completion of reaction
customUnreacted boron tribromide was destroyed
additionby adding methanol, solvent
customremoved
additionthe residual oil diluted with diethyl ether
washThe organic phase was washed with saturated NaHCO3, water and brine
customdried
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-fcc48195aafe4bc58d90fe2f92ee75b7
Quelldatensatz: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07169942B2

Verknüpfte Notizen

Wird geladen…