Sodium hydride → (E)-4-(4-methoxyphenyl)but-3-enoic acid

Temperature

0 °C

The mixture of (2-carboxyethyl)triphenylphosphonium bromide (20.0 g, 54.0 mmol) and 4-methoxybenzaldehyde (6.5 g, 53.5 mmol) in anhydrous DMSO (64 mL) was added slowly to the suspension of 60% NaH in mineral oil (4.3 g, 107 mmol) in anhydrous tetrahydrofuran (32 mL). The reaction mixture was stirred at 0° C. for 30 minutes then warmed to room temperature over 4 hours. The reaction mixture was quenched with 1N HCl (150 mL) and extracted with ethyl acetate. The organic phase was washed with water, brine, dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (50% EtOAc in hexanes) to provide (E)-4-(4-methoxyphenyl)but-3-enoic acid (557) (5.7 g, 55.0%) as a yellow solid.

1. temperaturethen warmed to room temperature over 4 hours
2. customThe reaction mixture was quenched with 1N HCl (150 mL)
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed with water, brine
5. dry with materialdried with sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash chromatography on silica gel (50% EtOAc in hexanes)

ORD record

ord-acebfbeec9024465921b93a880490b57

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476308B2