1-Heptyne → HCID 25221728, compound

HRID 451276Notes

Reaction equation

HRID 451276 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CCCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 86646625HCID 86646625, compound

Product 1

HCID 25221728HCID 25221728, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 3-chloro-5-fluoro-phenyl ester and 1-heptyne following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane; yield (110 mg, 98%); 1H NMR δ (CDCl3): 7.16 (s, 1H), 7.02-6.94 (m, 2H), 2.43 (t, J=7.13 Hz, 2H), 1.62 (p, J=7.12 Hz, 2H), 1.45-1.29 (m, 4H), 0.92 (t, J=7.22 Hz, 3H); LCMS m/z: 224.

Workup

  1. customyield (110 mg, 98%)

Sources & evidence

ORD record
ord-575432961f7946458abe0569d7beccd1
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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