5-Hexyn-1-ol → HCID 25221833, compound

HRID 451280Notes

Reaction equation

HRID 451280 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](OS(C1C=CC=CC=1)(=O)=O)[CH:7]=[CH:6]2)#[N:2].[CH2:23]([OH:29])[CH2:24][CH2:25][CH2:26][C:27]#[CH:28]>CCCCCCC.CCOC(C)=O>[OH:29][CH2:23][CH2:24][CH2:25][CH2:26][C:27]#[C:28][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([C:1]#[N:2])[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 702345-Hexyn-1-olHCID 86646626HCID 86646626, compound

Product 1

HCID 25221833HCID 25221833, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from benzenesulfonic acid 6-cyano-naphthalen-2-yl ester and hex-5-yn-1-ol following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 6:4; yield (90 mg, 72%); 1H NMR δ (CDCl3): 8.2 (s, 1H), 7.93 (s, 1H), 7.88-7.76 (m, 2H), 7.65-7.52 (m, 2H), 3.73 (t, J=7.20 Hz, 2H), 2.50 (t, J=7.22 Hz, 2H), 1.87-1.68 (br m, 5H); LCMS m/z: 249.

Workup

  1. customyield (90 mg, 72%)

Sources & evidence

ORD record
ord-78065cc7e42f4201b42142984f4d80c5
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

Loading…