5-Hexyn-1-ol → 6-(Quinolin-3-yl)hex-5-yn-1-ol

HRID 1967214Notes

Reaction equation

HRID 1967214 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:2]=1.[CH2:22]([OH:28])[CH2:23][CH2:24][CH2:25][C:26]#[CH:27]>CCCCCCC.CCOC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:27]#[C:26][CH2:25][CH2:24][CH2:23][CH2:22][OH:28])[CH:2]=1

Participants

4

Reactant 2

HCID 702345-Hexyn-1-olHCID 86646622HCID 86646622, compound

Product 1

HCID 135575496-(Quinolin-3-yl)hex-5-yn-1-ol

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid quinolin-3-yl ester and hex-5-yn-1-ol following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 6:4; yield (110 mg, 98%); 1H NMR δ (CDCl3): 8.89 (s, 1H), 8.21 (s, 1H), 8.11 (d, J=8.62 Hz, 1H), 7.80-7.68 (dm, 2H), 7.62-7.52 (m, 1H), 3.74 (t, J=7.17 Hz, 2H), 2.52 (t, J=7.13 Hz, 2H), 1.83-1.67 (br m, 5H); LCMS m/z: 225.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (110 mg, 98%)

Sources & evidence

ORD record
ord-5fc9a94d8bf04442a5e6bca046b583e5
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

Loading…