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

Temperature

23 °C

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.

1. customAfter removing excess O3
2. concentrationconcentrated in vacuo
3. customPurification of the residue via flash chromatography (silica gel 16 mL; 5→15% EtOAc in hexanes)

ORD record

ord-d90f51e58d144947a68ef4cdaf0da292

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309599B2