Cyclopropylacetylene → HCID 68539387, compound

HRID 1992921Notes

Reaction equation

HRID 1992921 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[CH:21]1([C:24]#[CH:25])[CH2:23][CH2:22]1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:21]1([C:24]#[C:25][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:23][CH2:22]1

Participants

6

Reactant 2

HCID 138823CyclopropylacetyleneHCID 10710352Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 68539387HCID 68539387, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Coupling of methyl 4-(methyloxy)-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate (77) (0.70 g, 2.23 mmol) with cyclopropyl acetylene (0.30 g, 4.46 mmol) using Pd(PPh3)2Cl2 and CuI in DMF at room temperature gave 0.49 g (96%) of the title compound (149) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.80-0.95 (m, 4H), 1.45-1.55 (m, 1H), 3.82 (s, 3H), 3.87 (s, 3H), 6.80 (dd, J1=8.9 Hz, J2=2.7 Hz, 1H), 6.96 (d, J=2.8 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 231 (M+H)+.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-7c56a57fb0214d09888f563ab11f1227
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…