Phosphorus trichloride → Retinoyl chloride

Retinoic acid (1.00 g, 0.0033 mol) was dissolved in anhydrous toluene (10 ml) and phosphorus trichloride (PCl3) (0.46 g, 0.0033 mol) was added dropwise thereto. The mixture was stirred for 15 hours at room temperature under nitrogen atmosphere and under the condition for light and moisture to be intercepted. The retinoic acid chloride solution thus obtained was added dropwise together with the retinol prepared in Preparation 1 (0.95 g, 0.0033 mol) and triethylamine (0.61 g, 0.0041 mol) to anhydrous methylene chloride (30 ml) over 20 minutes at 0° C. The reaction solution was then stirred for 5 hours at room temperature. The reaction solution was added to saturated aqueous sodium chloride solution (30 ml). The organic layer was separated, washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica gel 60 for cc part, Merk Co., mesh size 270–400, hexane/diethylether=9/1, v/v) to give 1.54 g (Yield 82%) of the pale yellow title compound. 1H NMR data of this compound were the same as those in Example 1.

ORDレコード

ord-23b7a9197b4f49329dd3559f8a1d458d

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07173062B2