Propanal → 2,4-Dimethyl-3-acetyl-5-n-Propyl-pyrrole

HRID 1834410Notes

Reaction equation

HRID 1834410 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8].I.[CH:12](=O)[CH2:13][CH3:14].CC1NC(C(OCC)=O)=C(C)C=1C>CCOCC.C(O)(=O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:12][CH2:13][CH3:14])=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 527PropanalHCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 24841Hydrogen iodideHCID 137479Ethyl 3,4,5-trimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 203732052,4-Dimethyl-3-acetyl-5-n-Propyl-pyrroleYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

2,4-Dimethyl-3-acetyl-pyrrole (1.02 g), acetic acid (15 ml), aqueous hydriodic acid (25ml) and propionaldehyde (1.74g), were stirred at 25° C. three hours under nitrogen. The work up was the same as that of 2,3,4-trimethyl-5-carbethoxy-pyrrole in Example 4 except that 2 × 50 ml ether were used. Recrystallization from benzene gave the product 0.786 g (59%) m.p. 157°-158°C.

Workup

  1. customRecrystallization from benzene

Sources & evidence

ORD record
ord-d080107f1784485ba4badc191f6a9788
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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