Quinoline → HCID 70148757, compound

HRID 1276466Notes

Reaction equation

HRID 1276466 reaction equation
[C:1]1([C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:31]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[N:10]=[CH:9]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 184283751-[1-triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne

Product 1

HCID 70148757HCID 70148757, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-[1-Triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne (6.8 g, 0.014 mol) was dissolved in dry ethyl acetate (100 ml). Lindlar catalyst (5%, 1.8 g Pd on CaCO3 poisoned with lead) and 15 mgs of quinoline were added. H2 was added to the reaction flask via a balloon. The reaction flask was evacuated and then refilled with H2 gas from the balloon 3 times. The reaction was left to stir at room temperature under the presence of H2 (1 atm) for 48 hours. The H2 gas was removed and the reaction mixture filtered through a pad of celite with ethyl acetate, the ethyl acetate was removed in vacuo to afford 6.75 g of 1-[1-triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-cis-3-hexene.

Workup

  1. additionH2 was added to the reaction flask via a balloon
  2. customThe reaction flask was evacuated
  3. additionrefilled with H2 gas from the balloon 3 times
  4. waitThe reaction was left
  5. customThe H2 gas was removed
  6. filtrationthe reaction mixture filtered through a pad of celite with ethyl acetate
  7. customthe ethyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-737071f0ccdd44d083a45532a6d458b7
Source dataset
uspto-grants-2000_12
Patent number
US06166060

Reaction notes

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