Dimethyl Sulfide → (S)-4-formylbut-3-yn-2-yl acetate

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A solution of 8 (392 mg, 1.83 mmol) in methanol (4.6 mL) was treated with O3 for 3 min at −78° C. After removing excess O3, the reaction was quenched by slow addition of methylsulfide (1.35 mL, 18.3 mmol) at −78° C. The resulting mixture was stirred for 1 h at −78° C. and for 1 h at 23° C., and then concentrated in vacuo. Purification of the residue via flash chromatography (silica gel 16 mL; 5→15% EtOAc in hexanes) afforded aldehyde 9 (208 mg, 81%) as a colorless oil.

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