Sodium hydride → HCID 66914783, compound
Reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([I:19])[CH:16]=[C:15]2[CH2:20][OH:21])(=O)=O)=CC=1.[H-].[Na+]>O1CCCC1>[I:19][C:17]1[CH:16]=[C:15]2[N:14]([CH:18]=1)[CH2:13][CH2:12][O:21][CH2:20]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-[2-(hydroxymethyl)-4-iodo-pyrrol-1-yl]ethyl 4-methylbenzenesulfonate (2.0 g, 4.79 mmol) in tetrahydrofuran (15 mL) was slowly added to a suspension of sodium hydride (120 mg, 60% dispersion in mineral oil; 4.75 mmol) in tetrahydrofuran (5 mL) and stirred at room temperature for 36 h. The reaction was quenched with water and extracted with diethyl ether. The combined organic phases were washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue which was purified by column chromatography over silica gel using 2% ethyl acetate in petroleum ether to afford 7-iodo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine (800 mg, 66%) as a colorless crystalline solid.