1-Heptyne → Methyl 2-(1-heptyn-1-yl)-4-(methyloxy)benzoate

HRID 1992894Notes

Reaction equation

HRID 1992894 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]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>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>[C:21]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 123501-HeptyneHCID 10710352Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 68536171Methyl 2-(1-heptyn-1-yl)-4-(methyloxy)benzoateYield 100.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Coupling of methyl 4-(methyloxy)-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate (77) (0.80 g, 2.55 mmol) with 1-heptyne (0.70 mL, 5.10 mmol) using Pd(PPh3)2Cl2 and CuI gave 0.67 g (˜100%) of compound 110 as a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.92 (t, J=7.3 Hz, 3H), 1.30-1.50 (m, 4H), 1.60-1.70 (m, 2H), 2.47 (t, J=7.2 Hz, 2H), 3.83 (s, 3H), 3.87 (s, 3H), 6.82 (dd, J1=8.9 Hz, J2=2.7 Hz, 1H), 6.99 (d, J=2.7 Hz, 1H), 7.89 (d, J=8.8 Hz, 1H).

Sources & evidence

ORD record
ord-e1884d3105b641558728dddf25c62e58
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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