HCID 19815343, compound → HCID 19815410, compound

HRID 653916Notes

Reaction equation

HRID 653916 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)[N:16]=[C:15]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][N:14]2[C:18]([CH2:19][OH:20])=[CH:17][N:16]=[C:15]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 19815343HCID 19815343, compound

Product 1

HCID 19815410HCID 19815410, compoundYield 110.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.00 g of 10% palladium/carbon and 1.00 g of 1-(4-benzyloxybenzyl)-2-butyl-4-chloro-5-hydroxymethyl imidazole in 20 mL of methanol was stirred at 25° for five minutes. Hydrogen gas was bubbled into the solution, and the mixture was stirred under hydrogen gas (1 atm.) at 25° for 2 hours. The mixture was filtered, and the resulting solution concentrated in vacuo to furnish 0.75 g of 1-(4-hydroxybenzyl)-2-butyl-5-hydroxymethylimidazole; NMR (200 Mhz, DMSO-d6): δ 9.75 (bs, 1H); 7.55 (s, 1H); 6.91 (A2B2, 4H); 5.80 (bs, 1H); 5.35 (s, 2H); 4.45 (s, 2H); 2.89 (t, 2H); 1.44 (quint, 2H); 1.21 (sext., 2H); 0.8 (t, 3H).

Workup

  1. customHydrogen gas was bubbled into the solution
  2. stirringthe mixture was stirred under hydrogen gas (1 atm.) at 25° for 2 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe resulting solution concentrated in vacuo

Sources & evidence

ORD record
ord-97bf2229f38b452cbcd17abe6623d6da
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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