Formaldehyde → HCID 57907659, compound

Temperature

-78 °C

To a 500 mL 3 neck flask equipped with magnetic stirrer, addition funnel, and nitrogen inlet was charged 10 grams (g) of 3-(pentyloxy)prop-1-yne (0.72 mmol), and 140 mL of dry ethyl ether. The reaction mixture was cooled to −78° C. with stirring followed by the dropwise addition of 37.5 mls (60 mmole) of 1.6M n-Butyl lithium solution in hexane. The temperature was adjusted to 0° C. and 5.4 g (180 mmole) of solid paraformaldehyde was added. The mixture was then stirred at ambient temperature overnight. Ether and water was added to the mixture and the ether layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under vacuum on a rotary evaporator. Isolated 9.44 g of a colorless liquid which was consistent with the desired structure upon analysis by 300 MHz 1H NMR.

1. customwas adjusted to 0° C.
2. stirringThe mixture was then stirred at ambient temperature overnight
3. customthe ether layer was separated
4. washwashed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under vacuum on a rotary evaporator

ORD record

ord-358a6860bedc4bd8bcf80f1d35dce09a

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426412B2