Water → HCID 18673383, Verbindung

1.06 ml of a 30% solution of sodium methoxide in methanol were added dropwise, at room temperature, to a solution of 374 μl of 2-mercaptoethanol in 5 ml of anhydrous methanol, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then added to a solution of 1.2 g of 1-chloro-2,5-tetradecadiyne in 6 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 crystallized on cooling. It was purified by recrystallization from a heptane/pentane mixture and then from a heptane/pentane/diisopropyl ether mixture. 3-Thia-5,8-heptadecadiyn-1-ol was thus isolated in the form of pale yellow flakes with a yield of 61%.

1. temperatureThe mixture was maintained
2. temperatureThe mixture was maintained
3. stirringunder stirring for 15 hours at room temperature
4. extractionextracted 3 times with ethyl ether
5. washThe combined organic phases were washed 3 times with water
6. dry with materialwith a saturated aqueous solution of NaCl before being dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under vacuum in a rotary evaporator
9. customThe oil thus obtained
10. customcrystallized
11. temperatureon cooling
12. customIt was purified by recrystallization from a heptane/pentane mixture

ORD-Eintrag

ord-8ec1325324d84402acc5c0e4399c2b45

Quelldatensatz

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06511670B1