Quinoline → HCID 15230863, compound

HRID 1646795Notes

Reaction equation

HRID 1646795 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[CH3:11][C:12]1[C:17](=[O:18])[C:16]([CH3:19])=[C:15]([CH3:20])[C:14](=[O:21])[C:13]=1[CH:22]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:23][CH2:24][CH2:25][C:26]#[C:27][CH2:28][OH:29]>C(OCC)(=O)C>[CH3:11][C:12]1[C:17](=[O:18])[C:16]([CH3:19])=[C:15]([CH3:20])[C:14](=[O:21])[C:13]=1[CH:22]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][OH:29]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 19088069HCID 19088069, compound

Product 1

HCID 15230863HCID 15230863, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Rindler catalyst (90 mg) and quinoline (15 μl) were added to a solution of 7-(3,5,6-trimethyl-1,4-benzoquinon 2-yl)-7-phenyl-2-heptyn -1-ol (1.01 g, 3.0 mmole) in ethyl acetate (20 ml), and catalytic reduction was carried out at room temperature. 3 Hours later, when absorption (73 ml) of hydrogen was almost stopped, the reaction was suspended and the catalyst was filtered out. The ethyl acetate was distilled off under reduced pressure, and the residue was chromatographed on a silica gel column to elute with isopropayl ether to give (Z)-7-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)-7-phenyl-2-hepten -1-ol (0.95 g, 94%). Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1.

Workup

  1. customwas carried out at room temperature
  2. custom3 Hours later, when absorption (73 ml) of hydrogen
  3. filtrationthe catalyst was filtered out
  4. distillationThe ethyl acetate was distilled off under reduced pressure
  5. customthe residue was chromatographed on a silica gel column
  6. washto elute with isopropayl ether

Sources & evidence

ORD record
ord-2eaaca48423b4171820f80dfd5d6123c
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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