5-Phenyl-1-pentyne → HCID 25221950, compound

HRID 1967197Notes

Reaction equation

HRID 1967197 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1OS(C1C=CC(C)=CC=1)(=O)=O)=[O:4].[CH2:21]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:22][CH2:23][C:24]#[CH:25]>CCCCCCC.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:25]#[C:24][CH2:23][CH2:22][CH2:21][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:4]

Participants

4

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 2808173HCID 2808173, compound

Product 1

HCID 25221950HCID 25221950, compound

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from 3-(toluene-4-sulfonyloxy)-thiophene-2-carboxylic acid methyl ester and pent-4-ynyl-benzene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 4:6; yield (114 mg, 80%); 1H NMR δ (CDCl3): 7.33 (d, J=4.93 Hz, 1H), 7.16-7.09 (m, 5H), 7.01 (d, J=4.95 Hz, 1H), 3.81 (s, 3H), 2.77 (t, J=7.11 Hz, 2H), 2.42 (t, J=7.16 Hz, 2H), 1.94 (p, J=7.22 Hz, 2H); LCMS m/z: 284.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (114 mg, 80%)

Sources & evidence

ORD record
ord-33c7c5aaf3f04dff82d693b160010e4b
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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