Tetrahydrofuran → HCID 54107390, compound

A suspension solution of ethyltriphenylphosphonium bromide (1079.3 mg, 2.907 mmol) in THF (10 mL) was cooled to 0° C. LHMDS (2.781 mL, 2.781 mmol, 1.0 M in THF) was added dropwise, and the mixture was stirred for 30 minutes. A solution of 3-formyl-benzoic acid methyl ester (415.0 mg, 2.528 mmol) in THF (2.5 mL) was then added dropwise, and the mixture was stirred for 10 minutes and then stirred at room temperature overnight. The reaction mixture was quenched by adding a saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3-propenyl-benzoic acid methyl ester as a yellow transparent oily substance (218.2 mg, 49%).

1. stirringthe mixture was stirred for 10 minutes
2. stirringstirred at room temperature overnight
3. customThe reaction mixture was quenched
4. additionby adding a saturated aqueous ammonium chloride solution
5. extractionextracted with ethyl acetate
6. washThe organic layer was sequentially washed with water and saturated brine
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-858dd05be4bd4d7e9f069277e7d7bcf3

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2