Potassium Phosphate, Tribasic → Methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate

HRID 2177344Notes

Reaction equation

HRID 2177344 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[CH2:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)[CH3:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][C:5]=2[C:7]([O:9][CH3:10])=[O:8])=[CH:23][CH:22]=1)[CH3:20]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734352Boronic acid, (4-ethylphenyl)-HCID 90418547Methyl 5-methyl-3-(((trifluoromethyl)sulfonyl)oxy)thiophene-2-carboxylate

Product 1

HCID 90418379Methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50-mL sealed tube (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed methyl 5-methyl-3-(((trifluoro methyl)sulfonyl)oxy)thiophene-2-carboxylate (1.7 g, 5.59 mmol), (4-ethylphenyl)boronic acid (1.0 g, 6.69 mmol), K3PO4 (3.84 g, 18.1 mmol), Pd(PPh3)4 (157 mg, 0.136 mmol), 1,4-dioxane (40 mL). The resulting solution was stirred overnight at 80° C. in an oil bath. The reaction progress was monitored by TLC/LCMS (ethyl acetate/petroleum ether=1:6). The solids were filtered out and washed by 20 mL ethyl acetate. Collected the organic phases and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 1.46 g (100%) of methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate as light yellow oil.

Workup

  1. customInto a 50-mL sealed tube (1 atm)
  2. custompurged
  3. temperaturemaintained with an inert atmosphere of nitrogen
  4. filtrationThe solids were filtered out
  5. washwashed by 20 mL ethyl acetate
  6. customCollected the organic phases
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 1.46 g (100%) of methyl 3-(4-ethylphenyl)-5-methylthiophene-2-carboxylate as light yellow oil

Sources & evidence

ORD record
ord-43bdae2a1bef4e3c9dfba5f358638831
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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