Formaldehyde → 2,3,4,5-Tetramethylpyrrole

HRID 1834409Notes

Reaction equation

HRID 1834409 reaction equation
CC1NC(C(OCC)=O)=C(C)C=1.I.C=O.[CH3:16][C:17]1[NH:18][C:19]([C:24](OCC)=O)=[C:20]([CH3:23])[C:21]=1[CH3:22]>CCOCC.C(O)(=O)C>[CH3:16][C:17]1[NH:18][C:19]([CH3:24])=[C:20]([CH3:23])[C:21]=1[CH3:22]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 24841Hydrogen iodideHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl esterHCID 137479Ethyl 3,4,5-trimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 704842,3,4,5-Tetramethylpyrrole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

2,4-Dimethyl-5-carbethoxy-pyrrole (1.64 g), acetic acid (25 ml), aqueous hydriodic acid (25 ml) and paraformaldehyde (0.589g), were heated at 95°-100° C. for three hours under nitrogen with stirring. The work up was the same as that of 2,3,4-trimethyl-5-carbethoxy-pyrrole in Example 4 except the 2 × 75 ml of ether was used and care was taken to avoid exposure of the product to air. It was purified by distillation (10 mm, 60° C.) to give 0.628 g (52%), m.p. 106°-108° C. (lit4 m.p. 111°-112° C.).

Workup

  1. distillationIt was purified by distillation (10 mm, 60° C.)
  2. customto give 0.628 g (52%), m.p. 106°-108° C. (lit4 m.p. 111°-112° C.)

Sources & evidence

ORD record
ord-5c8adf5c0bd942a6807bf945faa80846
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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