Pyridine → (S)-oct-1-yn-3-yl acetate

Temperature

55 °C

(S)-1-octyn-3-ol (100 g., 0.794 mole) is dissolved in pyridine (79 g., 1.0 mole) and acetic anhydride (81.6 g., 0.8 mole) is added dropwise with stirring during 1 hour. The temperature rises to 45° C. The solution is heated at 55° C. for 1 hour and then is cooled and poured into ice-cold 5% hydrochloric acid (200 ml.) providing a heterogeneous mixture which is extracted with ether. The organic extract is washed with water and saturated aqueous brine, dried over sodium sulfate, and filtered. Evaporation of the filtrate in vacuo at 40° to 50° C. yields a residual oil which is distilled to give the title compound (106.4 g., 80%), b.p. 91°-92° C./15 mm.; [α]D26 -79° (C 3.0, CHCl3).

1. customrises to 45° C
2. temperatureis cooled
3. customproviding a heterogeneous mixture which
4. extractionis extracted with ether
5. extractionThe organic extract
6. washis washed with water and saturated aqueous brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customEvaporation of the filtrate in vacuo at 40° to 50° C.
10. customyields a residual oil which
11. distillationis distilled

ORD record

ord-337a933fc38c4cfe8aabcc83c70fdfc9

Source dataset

uspto-grants-1978_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04102888