Trimethyl orthoformate → HCID 13746853, compound

To freshly prepared ethyl magnesium bromide (from 61 mmoles bromoethane and 63 mmoles magnesium) was added 1-decyne (50 mmoles) in diethyl ether (10 ml) dropwise at ambient temperature. The reaction mixture was then heated at reflux for 2 hours. After cooling the reaction mixture, trimethylorthoformate (75 mmoles) in diethyl ether (10 ml) was added and the resultant mixture heated to distill off the diethyl ether. The resultant paste was taken up in anhydrous toluene (50 ml) and heated at reflux for 1 hour. The reaction mixture was poured into saturated ammonium chloride (50 ml) and then extracted with diethyl ether (3×50 ml). The organic phase was washed with water (3×20 ml) and dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded the desired product as an oil.

1. temperatureThe reaction mixture was then heated
2. temperatureat reflux for 2 hours
3. additionwas added
4. distillationto distill off the diethyl ether
5. temperatureheated
6. temperatureat reflux for 1 hour
7. additionThe reaction mixture was poured into saturated ammonium chloride (50 ml)
8. extractionextracted with diethyl ether (3×50 ml)
9. washThe organic phase was washed with water (3×20 ml)
10. dry with materialdried over anhydrous magnesium sulfate
11. customEvaporation of the organic phase

ORD record

ord-9aa4a599ffac4524bd714a62afd62fbd

Source dataset

uspto-grants-1986_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04623535