Water → Methyl 3,8-dithia-5-heptadecynoate

関与物質

反応手順

2 ml of a 30% solution of sodium methoxide in methanol were added to a solution of 2 ml of nonanethiol in a 20 ml methanol/5 ml THF mixture, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then added to a solution of 2 g of methyl 7-chloro-3-thia-5-heptynoate in 20 ml of methanol, under an inert atmosphere. The mixture was maintained under stirring for 15 hours at room temperature and then the reaction medium was poured over 100 ml of acid water (98 ml of water+2 ml concentrated H2SO4) and then extracted 3 times with ethyl ether. The combined organic phases were washed 3 times with water and then with a saturated aqueous solution of NaCl before being dried (Na2SO4), filtered and concentrated under vacuum in a rotary evaporator. The oil thus obtained was chromatographed on a silica gel column (CH2Cl2/heptane 85/15) providing 2.1 g of methyl 3,8-dithia-5-heptadecynoate in the form of an orange-colored oil (yield 64%).

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