Citric Acid → HCID 178487492, compound

HRID 392579Notes

Reaction equation

HRID 392579 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[CH2:14]([Li])[CH2:15][CH2:16]C.[CH:19]([C:21]1[N:22]=[CH:23][N:24](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:25]=1)=[O:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCCCCC>[NH:24]1[CH:25]=[C:21]([C:19]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[CH:3]=2)([OH:20])[CH:15]([CH3:16])[CH3:14])[N:22]=[CH:23]1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 787862-Bromo-6-methoxynaphthaleneHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 178487492HCID 178487492, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-Bromo-6-methoxynaphthalene (30 g) was dissolved in THF (400 ml) and cooled to −78° C. A solution (1.6 M; 99 ml) of n-butyl lithium in hexane was added dropwise, and the mixture was stirred at −78° C. for 30 min. A solution (300 ml) of 4-formyl-1-trityl-1H-imidazol (38.9 g) in THF was slowly added dropwise. After stirring at −78° C. for 30 min, the reaction mixture was poured into 3% aqueous citric acid solution (600 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layer was combined and the mixture was washed with saturated brine, dried and concentrated. The residue was washed with ethyl acetate to give the title compound (35.0 g) as a colorless solid.

Workup

  1. stirringAfter stirring at −78° C. for 30 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe mixture was washed with saturated brine
  5. customdried
  6. concentrationconcentrated
  7. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-20e5d771f14d45b690271d4c31551114
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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