Quinoline → HCID 54684903, compound

HRID 1385030Notes

Reaction equation

HRID 1385030 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[OH:11][C:12]1[C:13](=[O:28])[O:14][CH:15]([CH2:18][CH2:19][C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]=1[OH:17]>C(O)C.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[OH:11][C:12]1[C:13](=[O:28])[O:14][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]=1[OH:17]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 54703388HCID 54703388, compound

Product 1

HCID 54684903HCID 54684903, compound

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 702EthanolSolvent

Procedure

Quinoline (70 μL, 0.6 mmol), 15 mg of 5% Pd/BaSO4 and 61 mg (0.25 mmol) of 3,4-dihydroxy-5-[(4-phenyl)-3-butynyl]-2(5H)-furanone were combined in 20 mL of ethanol and hydrogenated at atmospheric pressure until 12 mL (0.5 mmol) of H2 was consumed as measured by a H2O filled burette. The catalyst was removed by filtration through two #1 fluted filter papers and the solution was concentrated to a volume of about 5 mL, taken up in 50 mL of ether and washed with 3×15 mL of 5% aqueous HCl, 20 mL of H2O and 20 mL of brine, dried (MgSO4) and concentrated to provide 3,4-dihydroxy-5-(4-phenylbutanyl)-2(5H)-furanone as a brown wax: 1H NMR (acetone- d6) δ 7.28-7.13 (m, 5H), 4.66 (dd, J=3.4, 7.2 Hz, 1H), 2.62 (t, J=7.7, 2H), 2.00-1.93 (m, 1H), 1.69-1.42 (m, 5H); 13C NMR (acetone-d6) δ 170.7, 154.9, 143.3, 129.2, 129.1, 126.5, 118.6, 76.2, 36.3, 32.7, 32.1, 24.6. Anal Calcd for C14H16O4+0.25 H2O: C, 66.52; H, 6.58. Found: C, 66.71; H, 6.75.

Workup

  1. customwas consumed
  2. customThe catalyst was removed by filtration through two #1
  3. filtrationfluted filter papers
  4. concentrationthe solution was concentrated to a volume of about 5 mL
  5. washwashed with 3×15 mL of 5% aqueous HCl, 20 mL of H2O and 20 mL of brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a1399fadd9b74e1ba867d06d6314dcc2
Source dataset
uspto-grants-2001_07
Patent number
US06262073B1

Reaction notes

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