Acetaldehyde → 1-Cyclooct-2-enylethanol

Participants

Reaction Conditions

Reaction Steps

At −50° C., a solution of 3-bromo-cyclooctene (4.2 g, 22 mmol; prepared by reaction of cyclooctene with N-bromosuccinimide) and titanium(IV)isopropoxide (7.2 ml, 24 mmol, 1.1 eq.) in diethyl ether (100 ml) was treated with a 2M solution of isopropylmagnesium chloride in diethyl ether (49 mmol, 2.2 eq.). The resulting mixture was stirred 1.5 h at −50° C., treated with acetaldehyde (1 ml, 18 mmol, 0.8 eq.), stirred 1 h at −40° C., and treated with 2M aqueous HCl solution. After extraction with MTBE (2×100 ml), washing of the organic phases with water (2×200 ml) and aqueous NaCl solution (200 ml), and drying (MgSO4), the crude product (4.4 g) was purified by flash chromatography (hexane/MTBE 6:1) to give 0.7 g of 1-cyclooct-2-enylethanol (26%).

Provenance & Evidence