Acetic Acid → HCID 86654671, compound

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([I:19])[CH:16]=[C:15]2[CH:20]=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([I:19])[CH:16]=[C:15]2[CH2:20][OH:21])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

Procedure

2-(2-Formyl-4-iodo-pyrrol-1-yl)ethyl 4-methylbenzenesulfonate (2.1 g, 5.01 mmol) in ethanol (25 mL) was cooled to 0° C. and sodium borohydride (95 mg, 2.50 mmol) was added. After 30 min, the reaction mixture was allowed to warm to ambient temperature and stirred for a further 1 h, after which time acetic acid was added and the mixture was concentrated in vacuo. The residue was partitioned between water and dichloromethane and the organic phase was washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2-[2-(hydroxymethyl)-4-iodo-pyrrol-1-yl]ethyl 4-methylbenzenesulfonate (2.0 g, 95%) as a brownish crystalline solid.