تفاعل #6715

معادلة التفاعل

Triethylamine

ethyl 6-hydroxyhexanoate

methanesulfonyl chloride

→

product

المردود 85.3%

Ethyl 6-methylsulfonyloxyhexanoate

المردود 85.3%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture was filtered through silica gel
2. 2
   غسيلthe filtrate was washed successively with water, saturated NaHCO3, water and brine
3. 3
   تجفيفThe organics were dried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo to a pale yellow oil
6. 6
   أخرىFinal purification of the crude product

الإجراء التجريبي

A solution of non-polydispersed ethyl 6-hydroxyhexanoate (50.76 ml, 50.41 g, 227 mmol) in dry dichloromethane (75 ml) was chilled in a 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 non-polydispersed product (46.13 g, 85%) as a clear, colorless oil. FAB MS: m/e 239 (M+H), 193 (M−C2H5O).

المصدر