1-(18-(benzyloxy)octadecan-9-yl)-1H-imidazole → 10-(1H-imidazol-1-yl)octadecan-1-ol

HRID 2204039Notes

Reaction equation

HRID 2204039 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])C1C=CC=CC=1.[H][H]>CCO.[Pd]>[N:27]1([CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

5

Reactant 2

HCID 866916531-(18-(benzyloxy)octadecan-9-yl)-1H-imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 8669165410-(1H-imidazol-1-yl)octadecan-1-olYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(18-(benzyloxy)octadecan-9-yl)-1H-imidazole (1.5 g, 3.52 mmol) was dissolved in EtOH, then 10% Pd on carbon (200 mg) was added and the reaction mixture hydrogenated under hydrogen balloon at reflux for 2 days. The reaction was filtered off to remove Pd carbon, then the filtrate was concentrated. The crude product was purified by silica gel column (3% MeOH in DCM) to give 10-(1H-imidazol-1-yl)octadecan-1-ol as a gummy liquid (0.96 g, 81%).

Workup

  1. filtrationThe reaction was filtered off
  2. customto remove Pd carbon
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by silica gel column (3% MeOH in DCM)

Sources & evidence

ORD record
ord-adc2f61786b541acab937a156caeffee
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

Loading…