Tetrahydrofuran → HCID 178467483, compound

HRID 1758751Notes

Reaction equation

HRID 1758751 reaction equation
C([N:4]1[CH:8]=[C:7]([CH3:9])[N:6]=[CH:5]1)(=O)C.[O:10]1CC[CH2:12][CH2:11]1>>[C:11]([C:8]1[NH:4][CH:5]=[N:6][C:7]=1[CH3:9])(=[O:10])[CH3:12]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 109534921-Acetyl-4-methylimidazole

Product 1

HCID 178467483HCID 178467483, compoundYield 38%

Procedure

A solution of 5.0 g (40.3 mmol) of 1-acetyl-4-methylimidazole in 700 ml of dry tetrahydrofuran was photolyzed in a quartz flask with a short wave ultraviolet light source (254 nm) for 24 hours. The tetrahydrofuran solution was concentrated in vacuo to give an oil which was chromatographed on silica gel using 5% methanol in chloroform as eluent to give 1.91 g (38%) of 5-acetyl-4-methylimidazole as a white solid, mp 140°-142°. nmr (CDCl3 /D6DMSO) (δ): 7.45 (s, 1H); 2.52 (s, 3H); 2.48 (s, 3H).

Workup

  1. concentrationThe tetrahydrofuran solution was concentrated in vacuo
  2. customto give an oil which
  3. customwas chromatographed on silica gel using 5% methanol in chloroform as eluent

Sources & evidence

ORD record
ord-379ef8a2db034830b5dbdc158d8067c8
Source dataset
uspto-grants-1983_02
Patent number
US04374843

Reaction notes

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