4-Methylmorpholine → HCID 53760366, compound

Temperature

-10 °C

4-(Cyclohex-2-enyloxy)benzoic acid (25 g, 115 mmol) was dissolved in 250 mL dry tetrahydrofuran and cooled to -10° C. under an atmosphere of dry nitrogen. N-Methylmorpholine (12.6 mL, 115 mmol) and isobutylchloroformate (15.9 mL, 115 mmol) were added. After 10 minutes at -10° C., the mixture was warmed to room temperature and filtered. The volume was reduced to 50 mL under reduced pressure before cooling to 0° C. and adding diisobutylaluminum hydride (1.5M in toluene, 160 mL) over 10 minutes. After 30 minutes, the reaction was allowed to warm to ambient temperature and stirred for 2 hours. The mixture was cooled in an ice bath, diluted with ether, quenched with methanol, and poured into cold Rochelle's salt solution. The crude product was extracted with ether, dried over Na2SO4, and concentrated in vacuo. The residue obtained was chromatographed eluting with 20% ethyl acetate in hexane to give 4.24 g (18%) of the title alcohol.

1. temperaturethe mixture was warmed to room temperature
2. filtrationfiltered
3. temperaturebefore cooling to 0° C.
4. additionadding diisobutylaluminum hydride (1.5M in toluene, 160 mL) over 10 minutes
5. waitAfter 30 minutes
6. temperatureto warm to ambient temperature
7. temperatureThe mixture was cooled in an ice bath
8. additiondiluted with ether
9. customquenched with methanol
10. additionpoured into cold Rochelle's salt solution
11. extractionThe crude product was extracted with ether
12. dry with materialdried over Na2SO4
13. concentrationconcentrated in vacuo
14. customThe residue obtained
15. customwas chromatographed
16. washeluting with 20% ethyl acetate in hexane

ORD record

ord-6545934050254b01a1132ea181e193e4

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631401