Sodium Hydroxide → HCID 11196915, compound

HRID 854976Notes

Reaction equation

HRID 854976 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:13])[CH:12]=1)[O:9][CH:8]([C:14]([F:17])([F:16])[F:15])[C:7]([C:18]([O:20]CC)=[O:19])=[CH:6]2)[CH3:2].[OH-].[Na+]>CCO>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:13])[CH:12]=1)[O:9][CH:8]([C:14]([F:15])([F:16])[F:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]2)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69517330HCID 69517330, compound

Product 1

HCID 11196915HCID 11196915, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 6-ethyl-8-methyl-2- (trifluoromethyl)-2H-chromene-3-carboxylate (2.6 g, 8.3 mmol) in EtOH (90 mL), was added IN NaOH (24.8 mL, 24.8 mmol). The reaction was stirred at 25° C. for 18 h. The ethanol was removed from the reaction under reduced pressure. The residue was acidified with 2N HCl. The product was extracted into EtOAc (300 mL) then washed with brine (100 mL), dried over MgSO4, filtered, and concentrated. The crude product was dissolved in 20 mL EtOAc and then diluted with 150 mL hexane. The resulting solution was chilled at 0° C. for 30 min. The product, which precipitated from the solution, was collected by filtration. The desired product was isolated as an off-white solid in quantities of 1.6 g (68%). 1H NMR (DMSO-d6) 1.15 (t, 3H, J=7.56 Hz), 2.16 (s, 3H), 2.51 (q, 2H, J=7.6 Hz), 5.89 (q, 1H, J=7.4 Hz), 7.11 (d, 1H, J=2.1 Hz), 7.14 (d, 1H, J=2.1 Hz), 7.79 (s, 1H).

Workup

  1. customThe ethanol was removed from the reaction under reduced pressure
  2. extractionThe product was extracted into EtOAc (300 mL)
  3. washthen washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude product was dissolved in 20 mL EtOAc
  8. additiondiluted with 150 mL hexane
  9. temperatureThe resulting solution was chilled at 0° C. for 30 min
  10. customThe product, which precipitated from the solution
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-27b4f637b8e144ab9aa52e9bb532aad8
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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