Imidazole → 4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

Temperatur

20 °C

Triphenylphosphine (172 mmol, 45 g) and imidazole (172 mmol, 12 g) were dissolved in THF/acetonitrile (3:1, 300 ml). The mixture was cooled under an ice bath, and iodine (172 mmol, 44 g) was added in four portions with vigorous stirring over 20 minutes. The resulting slurry was warmed to 20° C. and then cooled to 0° C. (±)-2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanol (156 mmol, 25 g) was added dropwise to the reaction mixture over 15 minutes. The mixture was stirred at room temperature overnight. The mixture was concentrated, diluted with 5% sodium bicarbonate solution and extracted with hexane. The combined organic layer was dried with MgSO4 and concentrated. Silica gel chromatography gave 4-(2-iodo-ethyl)-2,2-dimethyl-[1,3]dioxolane as a clear oil; 1H NMR (400 MHz, CDCl3): δ 4.18-4.12 (m, 1H), 4.06 (dd, 1H, J=8.0 Hz, J2=6.1 Hz), 3.55 (dd, 1H, J1=8.0 Hz, J2=6.5 Hz), 3.28-3.17 (m, 2 H), 2.11-1.98 (m, 2H), 1.38 (s, 3H), 1.33 (s, 3H).

1. temperatureThe mixture was cooled under an ice bath
2. additionwas added dropwise to the reaction mixture over 15 minutes
3. stirringThe mixture was stirred at room temperature overnight
4. concentrationThe mixture was concentrated
5. additiondiluted with 5% sodium bicarbonate solution
6. extractionextracted with hexane
7. dry with materialThe combined organic layer was dried with MgSO4
8. concentrationconcentrated

ORD-Eintrag

ord-c543dedb27c84d1c9700f8c15aedf7c4

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07612106B2