Butyl oxoacetate → HCID 54056081, compound

Participants

Reaction Steps

To a solution of 21.6 mg (0.05 mmol) of a chiral titanium complex, (R)-1, in 3 ml of methylene chloride were added 157 mg (1 mmol) of Z-3-(trimethylsilyl)oxy-2-pentene and subsequently a solution of 130 mg (1 mmol) of freshly distilled butyl glyoxylate in 0.5 ml of methylene chloride at 0° C. After stirring for 30 minutes at that temperature, the resultant mixture was poured into 10 ml of a saturated sodium hydrogencarbonate aqueous solution at 0° C. The solution was filtered through a pad of Celite, and the filtrate was extracted three times with a 5 ml portion of diethyl ether. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. Separation by silica gel chromatography (eluent: hexane/ethyl acetate=15/1 by volume) gave 181 mg (0.63 mmol; yield 63%) of butyl 2-hydroxy-3-methyl-4-(trimethylsilyl)oxy-4-hexenoate.

Provenance & Evidence