3-Methyl-2-butenoic acid → HCID 67361782, compound

HRID 1911273Notes

Reaction equation

HRID 1911273 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](O)=[O:5].[F:8][C:9]([F:19])([F:18])[O:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[CH3:1][C:2]1([CH3:7])[CH2:3][C:4](=[O:5])[C:14]2[C:13](=[CH:12][C:11]([O:10][C:9]([F:8])([F:18])[F:19])=[CH:16][CH:15]=2)[O:17]1

Participants

4

Reactant 2

HCID 109313-Methyl-2-butenoic acid2×HCID 27332613-(Trifluoromethoxy)phenol

Product 1

HCID 67361782HCID 67361782, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent2×

Procedure

Eaton's reagent (225 mL) was heated to 70° C. and 3-methylbut-2-enoic acid (28.1 g, 281 mmol) and 3-(trifluoromethoxy)phenol (25.0 g, 140 mmol) were added. After 30 min, additional 3-methylbut-2-enoic acid (1 equiv, 14 g) was added and heating was continued. After 30 min, additional Eaton's reagent (150 mL) was added and heating was continued for 35 min. The dark solution was cooled and poured into ice. The aqueous suspension was extracted with Et2O (300 mL), and the organic portion was washed with water (75 mL) and brine (50 mL). The organic portion was dried (Na2SO4), filtered, concentrated, and purified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes) to give the title compound (11.7 g, 45.0 mmol, 32%) as a white solid. MS (ESI) m/z 261 (M+H)+.

Workup

  1. temperatureheating
  2. waitAfter 30 min
  3. temperatureheating
  4. waitwas continued for 35 min
  5. temperatureThe dark solution was cooled
  6. additionpoured into ice
  7. extractionThe aqueous suspension was extracted with Et2O (300 mL)
  8. washthe organic portion was washed with water (75 mL) and brine (50 mL)
  9. dry with materialThe organic portion was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custompurified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0e5d0151fbe34be2b9d4874e28412642
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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