Diisobutylaluminumhydride → [5-Bromo-4-ethyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol

HRID 554285Notes

Reaction equation

HRID 554285 reaction equation
[Br:1][C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([C:16](OC)=[O:17])[C:3]=1[CH2:20][CH3:21].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([CH2:16][OH:17])[C:3]=1[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66924922Methyl 5-bromo-4-ethyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 66924674[5-Bromo-4-ethyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanolYield 88.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using methyl 5-bromo-4-ethyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (1.35 g) and a 1.5 mol/L solution (7.5 mL) of diisobutylaluminum hydride in toluene, a procedure as in Reference Example 5 was performed to give the title compound as a brown oil (yield 1.10 g, 88%).

Sources & evidence

ORD record
ord-566c35ff4e9c4279ac57dc950728c970
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

Loading…