HCID 19815343, compound → HCID 19815308, compound

HRID 653914Notes

Reaction equation

HRID 653914 reaction equation
C([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][N:14]2[C:18]([CH2:19][OH:20])=[C:17]([Cl:21])[N:16]=[C:15]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:18]([CH2:19][OH:20])=[C:17]([Cl:21])[N:16]=[C:15]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 19815343HCID 19815343, compound

Product 1

HCID 19815308HCID 19815308, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.50 g of 1-(4-benzyloxybenzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole, 0.50 g of 10% palladium/carbon and 40 mL of tetrahydrofuran was stirred at room temperature under hydrogen gas (1 atm.) for 6 hours. The mixture was filtered through Celite® under nitrogen, and the resulting solution was concentrated in vacuo. The crude product was extracted with hot chloroform. After cooling, the chloroform mixture was concentrated in vacuo, and the resulting solid was washed with hexane to afford 0.16 g of 1-(4-hydroxybenzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole; NMR (200 MHz, DMSO-d6): δ 9.43 (s, 1H); 6.81 (A2B2, 4H); 5.21 (t, 1H); 5.10 (s, 2H); 4.33 (d, 2H); 2.47 (t, 2H); 1.44 (quint 2H); 1.23 (sext., 2H); 0.79 (t, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite® under nitrogen
  2. concentrationthe resulting solution was concentrated in vacuo
  3. extractionThe crude product was extracted with hot chloroform
  4. temperatureAfter cooling
  5. concentrationthe chloroform mixture was concentrated in vacuo
  6. washthe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-ebf7a08cee5546659027687285e6f474
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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