1-Heptyne → 1-Hept-1-ynyl-4-trifluoromethoxy-benzene

HRID 451271Notes

Reaction equation

HRID 451271 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.[CH:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CCCCCCC>[C:23]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:9][CH:8]=1)#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 18424495Toluene-4-sulfonic acid 4-trifluoromethoxy-phenyl ester

Product 1

HCID 252217231-Hept-1-ynyl-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-heptyne following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane; yield (100 mg, 78%); 1H NMR δ (CDCl3): 7.41 (d, J=8.55 Hz, 2H), 7.21 (d, J=8.56 Hz, 2H), 2.43 (t, J=7.21 Hz, 2H), 1.62 (p, J=7.16 Hz, 2H), 1.48-1.3 (m, 4H), 0.93 (t, J=7.22 Hz, 3H); LCMS m/z: 256.

Workup

  1. customyield (100 mg, 78%)

Sources & evidence

ORD record
ord-be51d8dd97714528b56a24a5759a2832
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

Loading…