Acetyl chloride → 2-Acetyl-1-furfurylpyrrole

HRID 1606212Notes

Reaction equation

HRID 1606212 reaction equation
[CH2:1]([N:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[C:12](Cl)(=[O:14])[CH3:13]>>[CH2:1]([N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12](=[O:14])[CH3:13])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 150371-Furfurylpyrrole

Product 1

HCID 205603682-Acetyl-1-furfurylpyrrole

Procedure

a. 1-furfuryl-2-acetyl-pyrrole was prepared starting from 1-furfuryl-pyrrole described by Reichstein in Helv. 15, 1450 (1932) as well as Gianturco et al. in Tetrahedron 207, 1763 (1964). Acetylation by reaction of the Grignard intermediate with acetyl chloride [cf. Chem. Ber. 47, 1416 (1914)] led to the desired ketone. (A small amount of the 3-isomer was also obtained, separable by fractional distillation). The product boils at 100°-102° C./0.03 mm Hg. and crystallizes on standing. Recrystallization from a mixture of methylene dichloride and petroleum ether gave a white crystalline product with a m.p. of 42°-43° C.

Workup

  1. custom(A small amount of the 3-isomer was also obtained, separable by fractional distillation)
  2. customand crystallizes
  3. customRecrystallization
  4. additionfrom a mixture of methylene dichloride and petroleum ether
  5. customgave a white crystalline product with a m.p. of 42°-43° C.

Sources & evidence

ORD record
ord-e24de316c2014603a3b6cad9a2cc846b
Source dataset
uspto-grants-1976_04
Patent number
US03952026

Reaction notes

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