Hydrochloric Acid → 4-(3-Fluorophenyl)-3-buten-1-ol

Temperature

0 °C

A mixture of 4.0 g of (3-hydroxypropyl)triphenylphosphonium bromide and 20 ml of tetrahydrofuran was cooled to 0° C., to which 12.5 ml of 1.6M n-butyl lithium (as a hexane solution) was slowly added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, to which a mixture of 1.24 g of 3-fluorobenzaldehyde and 10 ml of tetrahydrofuran was slowly added dropwise at the same temperature, followed by further stirring at room temperature for 6 hours. The reaction mixture was poured into ice-water, acidified by the addition of 10% hydrochloric acid, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.70 g of 4-(3-fluorophenyl)-3-buten-1-ol.

1. additionwas slowly added dropwise
2. additionwas slowly added dropwise at the same temperature
3. stirringby further stirring at room temperature for 6 hours
4. extractionextracted twice with 50 ml of diethyl ether
5. washThe combined ether layer was washed with saturated saline solution
6. dry with materialdried with anhydrous magnesium sulfate
7. concentrationconcentrated
8. customto obtain a crude product

ORD record

ord-1b580b44dd8a451f8b6b4ce8b4ab1c9a

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05872137