Methoxymethyl-triphenylphosphonium chloride → HCID 66782157, compound

Temperature

0 °C

Methoxymethyl triphenylphosphonium chloride (3.94 g, 11.5 mmol) was suspended in anhydrous THF (25 mL) under an atmosphere of dry N2. After cooling to 0° C., potassium tert-butoxide (1.41 g, 12.5 mmol) was added. The solution was stirred at 0° C. for 5 minutes, then warmed to ambient temperature. After 15 minutes 8-(tert-butyldimethylsilyloxy)quinoline-2-carbaldehyde (3.00 g, 10.4 mmol) was added. The reaction was stirred at ambient temperature overnight, and then concentrated under vacuum. Diethyl ether (200 mL) was added, and the mixture was stirred at ambient temperature for 1 hour and then filtered. The precipitate was washed with diethyl ether and the filtrate was collected and concentrated under vacuum. The resulting residue was dissolved in diethyl ether (50 mL) to which hexanes (50 mL) was added. The mixture was stirred for 1 hour and then filtered. The filtrate was concentrated under vacuum to give 3.12 g, 95% of the desired product as a mixture of cis-trans isomers.

1. temperaturewarmed to ambient temperature
2. stirringThe reaction was stirred at ambient temperature overnight
3. concentrationconcentrated under vacuum
4. additionDiethyl ether (200 mL) was added
5. stirringthe mixture was stirred at ambient temperature for 1 hour
6. filtrationfiltered
7. washThe precipitate was washed with diethyl ether
8. customthe filtrate was collected
9. concentrationconcentrated under vacuum
10. dissolutionThe resulting residue was dissolved in diethyl ether (50 mL) to which hexanes (50 mL)
11. additionwas added
12. stirringThe mixture was stirred for 1 hour
13. filtrationfiltered
14. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-b6f25ac6c3bb48c1ac0214b6e70e660d

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138181B2