Butyl oxoacetate → HCID 19922580, compound

Participants

Reaction Conditions

Reaction Steps

0.5 ml (0.1 mmol) of (R)-1 solution prepared in the same manner as in Example 1 were cooled to 0° C., and 190 mg (1 mmol) of (E)-1-ethylthio-1-trimethylsilyloxy-1-propene (77% E) and subsequently 130 mg (1 mmol) of freshly distilled butyl glyoxylate and 0.5 ml of toluene were added thereto, followed by allowing the mixture to react at 0° C. for 0.5 hour. The resulting mixture was poured into 10% hydrochloric acid-methanol cooled 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 a saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=15/1 by volume) to obtain 158 mg (yield 64%) of n-butyl 4-ethylthio-2-hydroxy-3-methyl-4-oxobutyrate.

Provenance & Evidence