1,4-Dimethyl-2-hydroxymethyl-(2'-nitrophenyl) pyrrole → 1,4-Dimethyl-3-(2'-nitrophenyl)pyrrole-carbaldehyde

HRID 2082379Notes

Reaction equation

HRID 2082379 reaction equation
C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.[CH3:9][N:10]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[C:11]1[CH2:25][OH:26]>O=[Mn]=O>[CH3:9][N:10]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[C:11]1[CH:25]=[O:26]

Participants

4

Reactant 2

HCID 159261931,4-Dimethyl-2-hydroxymethyl-(2'-nitrophenyl) pyrroleHCID 22996148Carbon tetrachloride methylene chloride

Product 1

HCID 159261941,4-Dimethyl-3-(2'-nitrophenyl)pyrrole-carbaldehydeYield 46.4%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

100 mg of MnO2, prepared according to Attenburrow's method, are suspended in a carbon tetrachloride/methylene chloride (4:1) mixture containing 500 mg of alcohol (12). The reaction medium is stirred at room temperature for 11/2 hours. The oxidizing agent is then filtered on celite. 230 mg of compound (13) are obtained (Yld:46%). This compound is purified by chromatography on a silica column (eluent:ethyl acetate/hexane, 1:1). It has the appearance of a yellow oil.

Workup

  1. filtrationThe oxidizing agent is then filtered on celite

Sources & evidence

ORD record
ord-8573741f84c54821997796310cf159fe
Source dataset
uspto-grants-1993_02
Patent number
US05189055

Reaction notes

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