Acetone → 2,4Dimethyl-3-acetyl-5-isopropyl pyrrole

HRID 1834422Notes

Reaction equation

[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8].[CH3:11][C:12]([CH3:14])=O.S(=O)(=O)(O)O>C(O)(=O)C.[Zn]>[CH3:1][C:2]1[NH:3][C:4]([CH:12]([CH3:14])[CH3:11])=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8]

Participants

Conditions

Temperature: 45 °C

Procedure

2,4-Dimethyl-3-acetyl-pyrrole (548 mg), 1 ml of acetone and 10 gm of amalgamated zinc (20 mesh) were added to a solution of 1 ml of concentrated sulfuric acid in 20 ml of acetic acid. The mixture was stirred for 1 hour at 45° C. The liquid was decanted from the zinc into 100 ml of water forming a solution from which the crude product separated at 15° C. (174 mg, m.p. 164°-169° C. after the usual solid phase changes). For analysis, it was extracted into ether (thimble) then recrystallized from 3 ml of aqueous ethanol as nearly colourless elongated prisms, m.p. 170°-172° C. (171°-173° when mixed with the product of Example 8) after a solid phase change at 142°. Anal. Calc. for C11H17NO: C, 73.70; H, 9.56; N, 7.81. Found: C, 73.60; H, 9.40; N, 7.92.

Workup

customThe liquid was decanted from the zinc into 100 ml of water forming a solution from which the crude product
customseparated at 15° C. (174 mg, m.p. 164°-169° C. after the usual solid phase changes)
extractionFor analysis, it was extracted into ether (thimble)
customthen recrystallized from 3 ml of aqueous ethanol as nearly colourless elongated prisms, m.p. 170°-172° C. (171°-173° when
additionmixed with the product of Example 8) after a solid phase change at 142°

Sources & evidence

ORD record: ord-4a08dd2964ee4de2b2a87cff1072d378
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04070366

Reaction notes

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