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

HRID 554292Notes

Reaction equation

HRID 554292 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([C:21](OC)=[O:22])[C:8]=2[CH2:25][CH2:26][CH3:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)(=[O:13])=[O:14])[CH:10]=[C:9]([CH2:21][OH:22])[C:8]=2[CH2:25][CH2:26][CH3:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66924675Methyl 5-phenyl-1-(phenylsulfonyl)-4-propyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66925059[5-Phenyl-1-(phenylsulfonyl)-4-propyl-1H-pyrrol-3-yl]methanolYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using methyl 5-phenyl-1-(phenylsulfonyl)-4-propyl-1H-pyrrole-3-carboxylate (3.0 g), and a 1.5 mol/L solution (16.1 mL) of diisobutylaluminum hydride in toluene, a procedure as in Reference Example 5 was performed to give the title compound as a pale-red oil (yield 2.73 g, 95%).

Sources & evidence

ORD record
ord-05d84c0e8fe24ca2bf12cef8485effe8
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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