Triethylamine → (E)-2-(3,3-Diethoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1270920

Reaktionsgleichung

[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].[CH3:10][C:11]1([CH3:18])[C:15]([CH3:17])([CH3:16])[O:14][BH:13][O:12]1.C(N(CC)CC)C>O1CCCC1.[H-].[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])/[CH:5]=[CH:6]/[B:13]1[O:14][C:15]([CH3:17])([CH3:16])[C:11]([CH3:18])([CH3:10])[O:12]1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 3,3-diethoxy-1-propyne (18.5 g, 0.144 mol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (27.6 g, 0.216 mol) and bis(cyclopentadienyl)zirconium chloride hydride (1.9 g, 0.007 mol) in tetrahydrofuran (75 mL) was heated at 50° C. for 2 days. Triethylamine (2 mL) was added and the solvent was removed in vacuo. The residue was distilled at 90° C. at 10 torr. The residue was purified by column chromatography on neutral alumina using 89:10:1 dichloromethane:ethyl acetate:triethylamine as an eluent. The solvent was removed in vacuo to give the title compound (15.9 g, 53%) as a brown oil. 1H NMR (DMSO-d6, 400 MHz) δ 6.48 (dd, 1H), 5.75 (d, 1H), 4.85 (d, 1H), 3.55–3.67 (m, 2H), 3.40–3.52 (m, 2H), 1.22 (s, 12H), 1.17 (t, 6H).

Aufarbeitung

customthe solvent was removed in vacuo
distillationThe residue was distilled at 90° C. at 10 torr
customThe residue was purified by column chromatography on neutral alumina using 89:10:1 dichloromethane
customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-df041ffd472e40d8a0d86260b88e10be
Quelldatensatz: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07202363B2

Verknüpfte Notizen

Wird geladen…