Quinoline → HCID 69069452, compound

HRID 1432820Notes

Reaction equation

HRID 1432820 reaction equation
[CH:1]1([CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH:9]2[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10]2)[CH2:3][CH2:2]1.N1C2C(=CC=CC=2)C=CC=1>CCCCCC.[Pd]>[CH:1]1([CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]2[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 58906751HCID 58906751, compound

Product 1

HCID 69069452HCID 69069452, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8058HexaneSolvent

Procedure

To a solution of 4-(5-Cyclopropyl-pent-3-ynyl)-2,2-dimethyl-[1,3]dioxolane (1.92 mmol, 0.40 g) in hexane (5 mL) was added quinoline (0.192 mmol, 24.8 mg), followed by addition of 5% Pd on BaSO4 (0.384 mmol). Stirred at room temperature under H2 atmosphere for 4 hrs. TLC showed reaction completed. Filtered through celite and concentrated. Diluted with hexane, washed with NH4Cl, brine and dried over MgSO4. Silica gel chromatography (2˜7% EtOAc/Hexane) 4-(5-Cyclopropyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane as clear oil 1H NMR (400 MHz, CDCl3): δ 5.52-5.45 (m, 1H), 5.40-5.34 (m,1H), 4.11-4.04 (m, 1H), 4.02 (dd, 1H, J1=8.0 Hz, J2=6.0 Hz), 3.51 (t, 1H, J=7.5 Hz), 2.17-2.04 (m, 2H), 1.97 (t, 2H, J=7.0 Hz), 1.74-1.66 (m, 1H), 1.58-1.49 (m, 1H), 1.41 (s, 3H), 1.35 (s, 3H), 0.73-0.68 (m, 1H), 0.43-0.39 (m, 2H), 0.08-0.04 (m, 2H).

Workup

  1. customreaction
  2. filtrationFiltered through celite
  3. concentrationconcentrated
  4. additionDiluted with hexane
  5. washwashed with NH4Cl, brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4c9883c2fde74b469bd06dd6f21740c7
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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