4-Methyl-1-trityl-1H-imidazole → HCID 19858075, compound

HRID 2073384Notes

Reaction equation

HRID 2073384 reaction equation
Br[CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]=[CH:8][C:9]3[O:10][C:11](=[O:18])[C:12]([CH3:17])([CH3:16])[C:13]=32)=[CH:5][CH:4]=1.[CH3:19][C:20]1[N:21]=[CH:22][N:23](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:24]=1>C(#N)C>[CH3:16][C:12]1([CH3:17])[C:11](=[O:18])[O:10][C:9]2[CH:8]=[CH:7][C:6]3[C:14]([C:13]1=2)=[CH:15][C:3]([CH2:2][N:21]1[C:20]([CH3:19])=[CH:24][N:23]=[CH:22]1)=[CH:4][CH:5]=3

Participants

4

Reactant 2

HCID 6182544-Methyl-1-trityl-1H-imidazoleHCID 19858042HCID 19858042, compound

Product 1

HCID 19858075HCID 19858075, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-bromomethyl-1,1-dimethyl-2(1H)-naphtho[2,1-b]furanone (0.46 g), 4-methyl-1-tritylimidazole (0.49 g) and acetonitrile (2 ml) was heated under reflux for 18 h, then evaporated to dryness. The residue was treated with glacial acetic acid (4 ml) and water (1 ml), and the mixture was heated at 90° for 0.5 h. The mixture was diluted with water (20 ml) and washed with diethyl ether. The aqueous phase was separated, basified with potassium hydrogen carbonate and extracted twice with ethyl acetate. The extracts were combined, dried and evaporated to dryness, and the residue was purified by flash chromatography, eluting with methanol:ethyl acetate, 1:99 v/v, to give 1,1-dimethyl-8-(5-methylimidazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone, m.p. 88°-91°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customevaporated to dryness
  4. additionThe residue was treated with glacial acetic acid (4 ml) and water (1 ml)
  5. temperaturethe mixture was heated at 90° for 0.5 h
  6. additionThe mixture was diluted with water (20 ml)
  7. washwashed with diethyl ether
  8. customThe aqueous phase was separated
  9. extractionextracted twice with ethyl acetate
  10. customdried
  11. customevaporated to dryness
  12. customthe residue was purified by flash chromatography
  13. washeluting with methanol

Sources & evidence

ORD record
ord-83f47eed0ffb4e6c9496abbb12638d08
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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