Imidazole → 5-(3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl)-4-methylisobenzofuran-1(3H)-one

Temperatur

25 °C

To a solution of 5-(2,3-dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one (2.00 g, 9.0 mmol) in dry DMF (20 mL) was added imidazole (1.20 g, 18.0 mmol) and TBSCl (1.50 g, 9.9 mmol). After stirring at 25° C. for 2.5 h, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with H2O (3×20 mL) and saturated NaHCO3 (3×20 mL). The combined aqueous layers were extracted five times with CH2Cl2 (20 mL). The combined organic layers were washed with brine (3×30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (0-60% ethyl acetate in petroleum ether) to give the title compound.

1. washwashed with H2O (3×20 mL) and saturated NaHCO3 (3×20 mL)
2. extractionThe combined aqueous layers were extracted five times with CH2Cl2 (20 mL)
3. washThe combined organic layers were washed with brine (3×30 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by flash column chromatography (0-60% ethyl acetate in petroleum ether)

ORD-Eintrag

ord-b2066a93780b4a7ca4a6c6bce8658d3f

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09206198B2