Acetic Acid → 3-TETRAHYDROPYRANYLOXY-1-TRIMETHYLSILYL-1-PROPYNE

Temperature

-20 °C

To a stirred -20° C. solution of 125 g (0.89 mol.) of 3-tetrahydropyranyloxy-1-propyne (Example 56) in 450 ml of ether, under a nitrogen atmosphere, is added dropwise, over one hour, a solution of 45 ml (0.89 mol.) of 2.0 N n-butyllithium in hexane. After 150 ml of dry ether is added and the mixture stirred at -20° C. for 30 minutes, a solution of 98 g (0.89 mol.) of trimethylchlorosilane in 73 ml of ether is added dropwise. Stirring is continued for 30 minutes at -20° C. and at ambient temperature for 18 hours. The reaction mixture is again cooled to -20° C., and a solution of 90 ml of acetic acid in 300 ml of ether is added dropwise, followed by 90 ml of water. It is then diluted with 500 ml of water, and extracted 3 times with 300 ml of 5% sodium bicarbonate solution. The organic phase is separated, washed with 500 ml of a saturated brine solution, dried over sodium sulfate, and evaporated at 40° C. under vacuum (12 mm.). The crude product is fractionally distilled, bp 120°-125° C. (18 mm.), to yield 120 g of an oil.

1. stirringStirring
2. waitis continued for 30 minutes at -20° C. and at ambient temperature for 18 hours
3. temperatureThe reaction mixture is again cooled to -20° C.
4. extractionextracted 3 times with 300 ml of 5% sodium bicarbonate solution
5. customThe organic phase is separated
6. washwashed with 500 ml of a saturated brine solution
7. dry with materialdried over sodium sulfate
8. customevaporated at 40° C. under vacuum (12 mm.)
9. distillationThe crude product is fractionally distilled

ORD record

ord-8fe512d7ef9d4f899e58f6a2696c35e7

Source dataset

uspto-grants-1980_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04202822