Acetonitrile → HCID 12816582, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH2:17][C:18]([OH:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:13]([O:25][Si](C(C)(C)C)(C)C)[CH2:12][C:11]1=[O:33].C(#N)C.F>O>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH2:17][C:18]([OH:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:13]([OH:25])[CH2:12][C:11]1=[O:33]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a Teflon container were placed (±)-methyl(16RS, 13E)-11-tert-butyldimethylsilyloxy-16-hydroxy-16-methyl-9-oxoprost-13-en-1-oate (1.89 g, 3.81 mmol) and acetonitrile (50 ml), whereby 46% hydrofluoric acid (4.5 ml) was added and stirred at room temperature for 2 h. The reaction mixture was added with water (120 ml) and extracted with methylene chloride (60 ml) two times. The combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate, a saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to remove solvent. The residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)] to give 1.44 g (99% yield) of Misoprostol;