Quinoline → 10-Undecen-1-ol

HRID 9797

Reaction equation

HRID 9797 reaction equation
[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCO>[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 7601510-Undecyn-1-ol

Product 1

HCID 818510-Undecen-1-olYield 101%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of undec-10-yn-1-ol (0.84 g, 5.0 mmol), quinoline (0.13 ml), Lindlar's catalyst (100 mg, 17% w/w) and EtOH (20 mL) was hydrogenated in a Parr apparatus at 50 psi of H2 for 1 h. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo to dryness to give undec-10-en-1-ol (0.86 g, 100%) as a colorless oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 5.78 (1H, m), 4.92 (2H, m), 3.61 (2H, t, J=6.6 Hz), 2.01 (2H, m), 1.53 (3H, m), 1.21–1.40 (12H, m); 13C NMR (75 MHz, CDCl3) δ 139.43, 114.31, 63.24, 34.00, 32.98, 29.74, 29.61, 29.31, 29.11, 25.92.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-86f52034622e4a4282757f1129537775
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Linked notes

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