2,3-Dihydroxybutanedioic Acid → HCID 15313893, compound

Participants

Reaction Conditions

Reaction Steps

Powdered, activated molecular sieves (4 Å, 1.80 g) were suspended in 205 ml of CH2Cl2 and the suspension was cooled to about -30° C. (+)-Diisopropyltartrate (0.76 ml, 0.06 eq.) and titanium (IV) isopropoxide (0.88 ml, 0.05 eq.) was added to the cooled suspension via syringe. A 3.8 M CH2Cl2 solution of t-butylhydroperoxide (4.4 ml, 0.28 eq.) was then added dropwise to the suspension over 5 min. while the temperature of the suspension was maintained between -20° C. and -30° C. After 30 min., a CH2Cl2 solution of trans-3-hepten-2-ol was added dropwise to the reaction mixture The reaction mixture was then held in the freezer (at -20° C.) for about 23 hours, after which it was warmed to 0° C. and poured onto a precooled (0° C.) solution of ferrous sulfate heptahydrate (19 g) and tartaric acid (6 g) in 6 ml of water. The resulting solution was stirred at room temperature for 10 min. The organic and aqueous phases were separated and the aqueous phase was extracted (2×38 ml) with ether. The organic layer and extracts were combined and vigorously stirred (0° C., 1 hour) after addition of 6 ml of a 30% (w/v) solution of NaOH in brine. After addition of 30 ml of water, the phases were separated and the aqueous phase was extracted (2×30 ml) with ether. The combined organic phases were dried over sodium sulfate. Evaporation of solvent, followed by flash chromatography of the residue (30% by volume ethyl acetate in hexane) gave a colorless liquid. The liquid was distilled to give 1(S)-methyl-2(S),3(S)-epoxyhexanol.

Provenance & Evidence