Ethyl 1,4-dimethyl-3-(2'-nitrophenyl)-2-pyrrolecarboxylate → 1,4-Dimethyl-2-hydroxymethyl-(2'-nitrophenyl) pyrrole

HRID 2082378Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[C:3]1[C:17](OCC)=[O:18].CC(C)=O.C(=O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[C:3]1[CH2:17][OH:18]

Participants

Conditions

Temperature: -78 °C

Procedure

200 mg (7) are dissolved in 30 ml of anhydrous methylene chloride and the solution is cooled to -78° C. in a bath (acetone/dry ice). 2.8 ml (4 equivalents) of 1M dibal in toluene are added dropwise. Stirring is maintained for 2 hours at -78° C., the flask is then removed from the cooling medium and 50 ml of aqueous (10%) sodium carbonate solution are introduced. A substantial emulsion appears, and is removed by filtration on celite. The clear organic phase collected is washed with water saturated with sodium chloride and dried over sodium sulfate. The alcohol (12) is purified on a silica column (120 mg ; Yld 71%).

Workup

customthe flask is then removed from the cooling medium and 50 ml of aqueous (10%) sodium carbonate solution
additionare introduced
customis removed by filtration on celite
customThe clear organic phase collected
washis washed with water saturated with sodium chloride
dry with materialdried over sodium sulfate
customThe alcohol (12) is purified on a silica column (120 mg ; Yld 71%)

Sources & evidence

ORD record: ord-7983115015a4437fac64340d0f2f81d7
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189055

Reaction notes

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