Potassium Carbonate → [8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

温度

100 °C

A mixture of (8-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate (0.49 g, 1.05 mmol), 2-chlorophenylboronic acid (0.33 g, 2.1 mmol), potassium carbonate (0.44 g, 3.2 mmol) and lithium chloride (0.13 g, 3.1 mmol) in dioxane (3.75 ml) and water (1.25 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.052 mmol) was added and the reaction mixture heated at 100° C. for 1 hour. The cooled reaction mixture was then partitioned between ethyl acetate (50 mL) and 1 M aqueous sodium hydroxide (50 mL). The organic layer was separated, washed with water (50 mL) dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford an orange oil. Purification by flash chromatography using a solvent gradient of 5 to 10% ethyl acetate in hexane gave 400 mg (89%) of [8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a white solid. HRMS: calcd for C23H21ClO4S+NH4+, 446.11873. found (ESI, [M+NH4]+), 446.1179.

1. customwas purged with nitrogen for 20 minutes
2. customThe cooled reaction mixture
3. customwas then partitioned between ethyl acetate (50 mL) and 1 M aqueous sodium hydroxide (50 mL)
4. customThe organic layer was separated
5. washwashed with water (50 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto afford an orange oil
10. customPurification by flash chromatography

ORDレコード

ord-a3693d14947d4322a9e066a5991d3ff5

出典データセット

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07365095B2