Ammonium Chloride → 4-(4,4,4-Trifluoro-but-1-enyl)-cyclohexanecarboxylic acid methyl ester

Temperature

0 °C

A 1.6 M solution of n-butyllithium in hexane (2.5 mL) was added dropwise to a suspension of triphenyl-(3,3,3-trifluoro-propyl)-phosphonium iodide (1.90 g, 3.91 mmol) in tetrahydrofuran (14 mL) at 0° C. The mixture was stirred at 0° C. for 35 minutes, and a solution of 4-formyl-cyclohexanecarboxylic acid methyl ester (605 mg, 3.55 mmol) in tetrahydrofuran (8.0 mL) was then added dropwise to the reaction solution at −78° C. The mixture was stirred for 45 minutes, and a saturated aqueous ammonium chloride solution was then added, followed by extraction with tert-butyl methyl ether. The organic layer was washed with water and a saturated aqueous sodium chloride solution and washed with sodium sulfate. After concentration, the residue was purified by silica gel column chromatography to give 4-(4,4,4-trifluoro-but-1-enyl)-cyclohexanecarboxylic acid methyl ester (657 mg, 67%) as a colorless oily substance and geometric isomer mixture.

1. stirringThe mixture was stirred for 45 minutes
2. extractionfollowed by extraction with tert-butyl methyl ether
3. washThe organic layer was washed with water
4. washa saturated aqueous sodium chloride solution and washed with sodium sulfate
5. concentrationAfter concentration
6. customthe residue was purified by silica gel column chromatography

ORD record

ord-b6f4bf81b9cc4eb38f2ba52753ea2943

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2