Tri-tert-butylphosphine tetrafluoroborate → 6-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydroisochromen-1-one

온도

85 °C

6-bromo-3,4-dihydro-1H-isochromen-1-one (10 g, 44 mmol) was combined with tri-t-butyl phosphonium tetrafluoroborate (256 mg, 0.881 mmol), palladium (II) acetate (99 mg, 0.44 mmol) and commercially available bromo(1,3-dioxolan-2-ylmethyl)zinc solution (0.5 M, 97 mL, 48 mmol) in DMF (100 mL), and the mixture was degassed three times by alternating vacuum and nitrogen purge. The mixture was then heated at 85° C. for 6 h, then was stirred at RT overnight. Ethyl acetate and ether were added and the mixture was washed with water. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, and washed twice with water and once with brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by MPLC (silica) eluting with ethyl acetate in hexanes to afford the title compound. LCMS: m/z 235 (M+1)+.

1. customthe mixture was degassed three times
2. custompurge
3. additionEthyl acetate and ether were added
4. washthe mixture was washed with water
5. extractionThe aqueous layer was extracted with ethyl acetate
6. washwashed twice with water and once with brine
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified by MPLC (silica)
11. washeluting with ethyl acetate in hexanes

ORD 기록

ord-5cb41f3a357142578481943aedb1d0e3

출처 데이터셋

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08999990B2