Methyltriphenylphosphonium iodide → N-(5-Chloro-3-methylidene-2,3-dihydro-1-benzofuran-4-yl)-2,2,2-trifluoroacetamide

To a mixture of potassium tert-butoxide (2.0) and methyltriphenylphosphonium iodide (7.1 g) was added dry toluene (70 ml) and the mixture stirred at room temperature for 30 min, then heated under reflux for 30 min. The mixture was cooled to room temperature, a solution of Intermediate 22 (1.0 g) in toluene (30 ml) added dropwise and the mixture heated under reflux for 30 min. The mixture was cooled and quenched by the dropwise addition of saturated ammonium chloride solution. The mixture was partitioned between ethyl acetate and water and the organic phase washed with water. The combined aqueous layers were re-extracted with ethyl acetate and the combined organic layers dried over sodium sulphate and concentrated in vacuo to give a dark brown oil. Purification by column chromatography on silica gel, eluting with 10% ethyl acetate in cyclohexane, gave the title compound as a rose coloured solid (0.5 g).

1. temperatureheated
2. temperatureunder reflux for 30 min
3. temperatureThe mixture was cooled to room temperature
4. temperaturethe mixture heated
5. temperatureunder reflux for 30 min
6. temperatureThe mixture was cooled
7. customquenched by the dropwise addition of saturated ammonium chloride solution
8. customThe mixture was partitioned between ethyl acetate and water
9. washthe organic phase washed with water
10. extractionThe combined aqueous layers were re-extracted with ethyl acetate
11. dry with materialthe combined organic layers dried over sodium sulphate
12. concentrationconcentrated in vacuo
13. customto give a dark brown oil
14. customPurification by column chromatography on silica gel
15. washeluting with 10% ethyl acetate in cyclohexane

ORD-Eintrag

ord-1368f349ddde440a9dc52c3212aec625

Quelldatensatz

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07566786B2