Acetone → HCID 22857740, compound

Participants

Reaction Conditions

Reaction Steps

To a frozen solution of the acid of Example 14, Step 7 (2.216 g, 4.28 mmol) in 30 mL of THF at -100° C. was added 1.6M BuLi in hexanes (5.9 mL) and the mixture was stirred at -78° C. for 30 min. Acetone (630 μL, 8.6 mmol) was then added and the mixture was stirred at -78° C. for 1 hr. and was then allowed to warm to -20° C. Saturated aq. NH4Cl was then added and the products were extracted in EtOAc. At 0° C., diazomethane ~0.5M was added. When the esterification was completed, the excess of CH2N2 was quenched with AcOH. The solution was dried over Na2SO4, concentrated and stripped with toluene. Hash chromatography of the residue with EtOAc:hexane 15:85 to 35:65 afforded first, the reduced starting material (desbromo), second, the product of addition of acetone α to the ester and third, the title product.

Provenance & Evidence