1-Heptyne → HCID 11073891, compound

HRID 1967207Notes

Reaction equation

HRID 1967207 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:2]=1.[CH:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CCCCCCC.CCOC(C)=O>[C:18]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 1712496HCID 1712496, compound

Product 1

HCID 11073891HCID 11073891, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid pyridin-3-yl ester and 1-heptyne following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 8:2; yield (60 mg, 70%); 1H NMR δ (CDCl3): 8.62-8.63 (m, 1H), 8.48-8.46 (m, 1H), 7.68-7.64 (m, 1H), 7.21-7.17 (m, 1H), 2.46 (t, J=7.21 Hz, 2H), 1.63 (p, J=7.15 Hz, 2H), 1.49-1.3 (m, 4H), 0.93 (t, J=7.22 Hz, 3H); LCMS m/z: 173.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (60 mg, 70%)

Sources & evidence

ORD record
ord-b2c21e48ec314b839f213bb7edc9f62f
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

Loading…