Hydrogen iodide → HCID 15020365、化合物

反応式

[CH:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I.[P]>C(O)(=O)C>[CH:1]1([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

実験手順

A mixture of the free base of α-cyclohexyl-α-(4-fluorophenyl) -4-pyridinemethanol (16.54 g, 0.058 mole), 57% hydrogen iodide (250 ml), glacial acetic acid (250 ml), and phosphorus (50.0 g) was heated overnight at reflux. The reaction mixture was cooled and filtered with Celite®. The volume of the filtrate was concentrated to 100 ml. Ice/50% sodium hydroxide was added and the aqueous phase was extracted with chloroform. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give a green oil. A 4 g portion of this oil was subjected to flask chromatography on silica gel using 20% ethyl acetate-hexanes for elution. Fractions of similar purity were combined and solvent removed to give an oil. This oil was dried in vacuo overnight at 80° C. The oil crystallized to give 2.95 g (33.9% yield) of white, crystalline solid, m.p. 78°-81° C.