1-Ethynylcyclohexene → 1-Cyclohex-1-enylethynyl-4-trifluoromethoxy-benzene

HRID 451273Notes

Reaction equation

HRID 451273 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:6][CH:5]=1.[C:23]([C:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1)#[CH:24]>CCCCCCC>[C:25]1([C:23]#[C:24][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:9][CH:8]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1

Participants

4

Reactant 2

HCID 791281-EthynylcyclohexeneHCID 18424495Toluene-4-sulfonic acid 4-trifluoromethoxy-phenyl ester

Product 1

HCID 252217251-Cyclohex-1-enylethynyl-4-trifluoromethoxy-benzene

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 4-trifluoromethoxy-phenyl ester and 1-ethynyl-cyclohexene following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane; yield (110 mg, 83%); 1H NMR δ (CDCl3): 7.41 (d, J=8.38 Hz, 2H), 7.21 (d, J=8.37 Hz, 2H), 6.28 (m, 1H), 2.17 (dm, 4H), 1.63 (dm, 4H); LCMS m/z: 266.

Workup

  1. customyield (110 mg, 83%)

Sources & evidence

ORD record
ord-a443adc7d1514c58a3542ae3902bad31
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

Loading…