5-Phenyl-1-pentyne → HCID 25222177, compound

HRID 1967210Notes

Reaction equation

HRID 1967210 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:2]=1.[CH2:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:19][CH2:20][C:21]#[CH:22]>CCCCCCC.CCOC(C)=O>[C:23]1([CH2:18][CH2:19][CH2:20][C:21]#[C:22][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 1712496HCID 1712496, compound

Product 1

HCID 25222177HCID 25222177, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid pyridin-3-yl ester and pent-4-ynyl-benzene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 8:2; yield (80 mg, 72%); 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, 6H), 2.76 (t, J=7.11 Hz, 2H), 2.4 (t, J=7.10 Hz, 2H), 1.91 (p, J=7.12 Hz, 2H); LCMS m/z: 221.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (80 mg, 72%)

Sources & evidence

ORD record
ord-3c6eb2ce66884eff8b3eaa55a08093ad
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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