Acetone → Methyl 2,3-dihydro-5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylate

23.3 g of methyl iodide and 7.6 g of potassium carbonate were added to a mixture of 7.8 g of 6C, 200 ml of acetone and 50 ml of dimethylsulfoxide. The resulting suspension was heated under reflux for 2 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was stirred with 400 ml of water, the water was decanted, and the residue was dissolved in tetrahydrofuran. The solution was filtered and the filtrate was concentrated. The residue was mixed with 50 g of silica gel and purified by dry column chromatography, a 9/1 v/v chloroform/tetrahydrofuran mixture being used as eluent. The band containing product was extracted with tetrahydrofuran, the solvent was evaporated from the extract under reduced pressure and the residue was dried in a vacuum oven. The residue was stirred with ether and the solid was collected and dried to give methyl 2,3-dihydro-5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylate (6D), mp: 98°-100° C.

1. temperatureThe resulting suspension was heated
2. temperatureunder reflux for 2 hours
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. customthe water was decanted
6. dissolutionthe residue was dissolved in tetrahydrofuran
7. filtrationThe solution was filtered
8. concentrationthe filtrate was concentrated
9. additionThe residue was mixed with 50 g of silica gel
10. custompurified
11. customby dry column chromatography
12. additionThe band containing product
13. extractionwas extracted with tetrahydrofuran
14. customthe solvent was evaporated from the
15. extractionextract under reduced pressure
16. customthe residue was dried in a vacuum oven
17. stirringThe residue was stirred with ether
18. customthe solid was collected
19. customdried

ORD record

ord-3f24fccff9df4532bd2a6ead6b5ffdc7

Source dataset

uspto-grants-1980_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04205080