Tetrahydrofuran → Acequinocyl

Participants

Reaction Steps

First, 0.60 g (4.4 mmoles) of ZnCl2 was dissolved in 20 mL of THF, and 6.30 g (4.39 mmoles, 0.697 mmoles/g) of dodecyl MgBr was added dropwise. After stirring for 15 minutes, this Zn reagent was added dropwise to 1.00 g (4.0 mmoles) of 2-acetoxy-3-chloro-1,4-naphthoquinone in 50 mL of THF. The mixture was stirred overnight and then poured into 100 mL of NH4Cl solution, extracted with 3×100 mL of ether, dried over MgSO4, filtered, and solvent was removed. The residue was flash-chromatographed to give 2-dodecyl-3-chloro-1,4-naphthoquinone and 2-dodecyl-3-acetoxy-1,4-naphthoquinone. The dodecylchloro derivative was recrystallized from hot ethanol; 0.217 g (0.603 mmoles, 15%). The dodecylacetoxy derivative was further purified by preparative TLC; 0.079 g (0.21 mmoles, 5%) mp: 49° to 51° C. (lit: 57° to 58° C.). 1H NMR (CDCl3, δ): 8.3 (m, 2H), 7.75 (m, 2H), 2.58 (m, 2H), 2.40 (s, 3H), 1.30 (br s, 20H), 0.9 (m, 3H). IR (CHCl3, cm-1): 2935s, 2860m, 1775s, 1679s, 1670sh, 1640m, 1600 m.

Provenance & Evidence