Triethylamine → Ethyl 6-methylsulfonyloxyhexanoate

A solution of monodispersed ethyl 6-hydroxyhexanoate (50.76 ml, 50.41 g, 227 mmol) in dry dichloromethane (75 ml) was chilled in an ice bath and placed under a nitrogen atmosphere. Triethylamine (34.43 ml, 24.99 g, 247 mmol) was added. A solution of methanesulfonyl chloride (19.15 ml, 28.3 g, 247 mmol) in dry dichloromethane (75 ml) was added dropwise from an addition funnel. The mixture was stirred for three and one half hours, slowly being allowed to come to room temperature as the ice bath melted. The mixture was filtered through silica gel, and the filtrate was washed successively with water, saturated NaHCO3, water and brine. The organics were dried over Na2SO4, filtered and concentrated in vacuo to a pale yellow oil. Final purification of the crude product was achieved by flash chromatography (silica gel, 1/1 hexanes/ethyl acetate) to give the monodispersed compound 2 (46.13 g, 85%) as a clear, colorless oil. FAB MS: m/e 239 (M+H), 193 (M-C2H5O).

1. filtrationThe mixture was filtered through silica gel
2. washthe filtrate was washed successively with water, saturated NaHCO3, water and brine
3. dry with materialThe organics were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo to a pale yellow oil
6. customFinal purification of the crude product

ORD record

ord-156f5d00d46c4d0d8dcce898d4106ca0

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867183B2