Acetic Acid → 2,3,4,5-Tetramethylpyrrole

HRID 1834435Notes

Reaction equation

[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[CH3:7].I.[PH2](O)=O.C=O.[C:14](O)(=O)[CH3:15]>>[CH3:5][C:4]1[NH:3][C:2]([CH3:1])=[C:6]([CH3:7])[C:14]=1[CH3:15]

Participants

Reactant 5

HCID 176Acetic Acid

HCID 712Formaldehyde

HCID 24841Hydrogen iodide

HCID 395382,3-Dimethyl-1H-pyrrole

HCID 4124402Phosphinic Acid

Product 1

HCID 704842,3,4,5-TetramethylpyrroleYield 51%

Procedure

As in Example 58, using 2,3-dimethyl-pyrrole (2 g), acetic acid (50 ml), hydriodic acid (50 ml), hypophosphorous acid (5 ml) and paraformaldehyde (1.2 g). Yield 51%, m.p. 105°-107°. Anal. Found: C, 77.81; H, 10.32; N, 11.45.

Sources & evidence

ORD record: ord-0f82ebb6f59d4fde8cd668a440f67c1f
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04070366

Reaction notes

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