1-Ethynylcyclohexene → HCID 25221837, compound

HRID 1967190Notes

Reaction equation

HRID 1967190 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4](OS(C2C=CC(C)=CC=2)(=O)=O)=[N:3]1.[C:22]([C:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1)#[CH:23]>CCCCCCC.C(Cl)Cl>[C:24]1([C:22]#[C:23][C:4]2[CH:5]=[C:6]([C:7]([F:8])([F:9])[F:10])[N:2]([CH3:1])[N:3]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1

Participants

4

Reactant 2

HCID 791281-EthynylcyclohexeneHCID 44543018HCID 44543018, compound

Product 1

HCID 25221837HCID 25221837, compound

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl ester and 1-ethynyl-cyclohexene following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 7:3; yield (80 mg, 63%); 1H NMR δ (CDCl3): 6.63 (s, 1H), 6.27-6.29 (m, 1H), 3.96 (s, 3H), 2.14-2.22 (m, 4H), 1.73-1.58 (m, 4H); LCMS m/z: 254.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (80 mg, 63%)

Sources & evidence

ORD record
ord-cab99d3c626449dbb227f30879faac21
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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