Реакция #739113

Уравнение реакции

para-Toluenesulfonyl chloride

1,5-dimethyl-8oxabicyclo[3.2.1]oct-6-en-3-ol

hydrochloric acid

→

desired product

Выход 88.0%

1,5-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-yl p-Toluenesulfonate

Выход 88.0%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   workup.WAITto stand in a refrigerator (0° C.) for 72 hours
2. 2
   workup.STIRRINGAfter stirring for 10 minutes
3. 3
   Фильтрацияthe precipitated solid was filtered
4. 4
   workup.DISSOLUTIONThe collected solid dissolved methylene chloride
5. 5
   Сушкаwas dried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated

Методика

para-Toluenesulfonyl chloride (15.5 g, ) was added portionwise over 20 minutes to an ice-cold stirred solution of 1,5-dimethyl-8oxabicyclo[3.2.1]oct-6-en-3-ol (10.0 g, ) in dry pyridine (75 ml). The reaction mixture was stirred at 0° C. for 0.5 hour, allowed to stand in a refrigerator (0° C.) for 72 hours, and poured into a mixture of 80 ml concentrated hydrochloric acid and 100 g of ice. After stirring for 10 minutes, the precipitated solid was filtered. The collected solid dissolved methylene chloride was dried (MgSO4), filtered and concentrated to give 17.6 g (88%) of the desired product, m.p. 75°-77° C., as a 70:30 mixture of epimers.

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