4-Methylmorpholine → 7,8-Methylenedioxy-4-chromanone

To a solution of 2,3-methylenediexyphenol (27 g) and N-methyl morpholine (19.6 g) in THF (100 ml) was added benzyl propiolate (38 g) over a period of 30 minutes with cooling. After the addition was complete the reaction was stirred at room temperature for 1.5 hours followed by concentration. The residue was taken up into Et2O (500 ml), washed with 10% HCl (2×100 ml), dried over MgSO4, filtered and concentrated. This material was subjected to hydrogenation with 10% Pd/C in methanol at 4 atm. The reaction was filtered and concentrated. The resulting saturated acid was dissolved into methanesulfonic acid (350 ml) and stirred for 24 hours. The reaction was poured onto ice and extracted with CH2Cl2. The organic layer was washed with saturated Na2CO3, dried over MgSO4, filtered and concentrated to provide the desired material.

1. temperaturewith cooling
2. additionAfter the addition
3. concentrationfollowed by concentration
4. washwashed with 10% HCl (2×100 ml)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. filtrationThe reaction was filtered
9. concentrationconcentrated
10. dissolutionThe resulting saturated acid was dissolved into methanesulfonic acid (350 ml)
11. stirringstirred for 24 hours
12. additionThe reaction was poured onto ice
13. extractionextracted with CH2Cl2
14. washThe organic layer was washed with saturated Na2CO3
15. dry with materialdried over MgSO4
16. filtrationfiltered
17. concentrationconcentrated

ORD record

ord-2cc453b7215542c996cd062ce3161c8e

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05140039