Ammonium Chloride → HCID 178450034, compound

HRID 480473Notes

Reaction equation

HRID 480473 reaction equation
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]([Li])(C)([CH3:9])[CH3:8].[CH:12]([C:14]1[CH:26]=[CH:25][C:24]2[C:16](=[CH:17][C:18]3[CH2:22][CH2:21][O:20][C:19]=3[CH:23]=2)[CH:15]=1)=[O:13].[Cl-].[NH4+]>C1COCC1.CCCCC>[CH2:22]1[CH2:21][O:20][C:19]2[CH:23]=[CH:24][C:25]3[C:17]([C:18]1=2)=[CH:16][CH:15]=[C:14]([C:12]([C:2]1[N:3]=[CH:4][NH:5][CH:6]=1)([OH:13])[CH:7]([CH3:9])[CH3:8])[CH:26]=3

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 187690466-Formyl-2,3-dihydronaphtho[2,3-b]furaneHCID 178418306HCID 178418306, compoundHCID 178418934HCID 178418934, compound

Product 1

HCID 178450034HCID 178450034, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 4-bromo-1H-imidazole (2.11 g) in THF (40 ml) was cooled to −78° C. A solution of tert-butyllithium in pentane (1.7 M; 13 ml) was added to the solution. The mixture was stirred at 5° C. for 2 h and then cooled to −78° C. 6-formyl-2,3-dihydronaphtho[2,3-b]furane (1.46 g) in THF (30 ml) was added to the mixture. The mixture was allowed to room temperature and was stirred for 20 h. Ammonium chloride solution was added to the mixture and extracted with mixed solution of THF and ethyl acetate. The organic layer was dried and concentrated. The residue was purified by silica gel chromatography to give the titled compound (1.01 g) as a colorless solid.

Workup

  1. temperaturecooled to −78° C
  2. customwas allowed to room temperature
  3. stirringwas stirred for 20 h
  4. extractionextracted with mixed solution of THF and ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d4abd5b775264e6093eba6c02eaf20f0
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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