Methyl 2-furoate → HCID 37979348, compound

Temperature

0 °C

Furan-2-carboxylic acid methyl ester (500 mg, 3.97 mmol) and 1-bromo-adamantane (853 mg, 3.97 mmol) were dissolved in ortho-dichlorobenzene (6 ml) and cooled to 0° C. before adding AlCl3 (1.06 g, 7.94 mmol) as a solid. The reaction mixture was allowed to warm up to room temperature, stirred for 4 h, then heated to 40° C. for 2 h and left standing at room temperature overnight. The reaction mixture was cooled to 0° C. and quenched with H2O (10 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×20 ml). The combined organic layers were dried (MgSO4), filtered and the DCM removed in vacuo. The ortho-dichlorobenzene solution was loaded to a silica-gel column and flushed with heptane (100 ml). The title compound was then eluted using a stepped gradient of 0-10% EtOAc in heptane.

1. temperatureto warm up to room temperature
2. temperatureheated to 40° C. for 2 h
3. waitleft
4. waitstanding at room temperature overnight
5. temperatureThe reaction mixture was cooled to 0° C.
6. customquenched with H2O (10 ml)
7. customThe organic layer was separated
8. extractionthe aqueous layer was extracted with DCM (3×20 ml)
9. dry with materialThe combined organic layers were dried (MgSO4)
10. filtrationfiltered
11. customthe DCM removed in vacuo
12. customflushed with heptane (100 ml)
13. washThe title compound was then eluted

ORD record

ord-688a6e75ba414fdc8b7d6f8bd24a5c4f

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662839B2