Sodium Hydroxide → HCID 21883526, compound

HRID 2214891Notes

Reaction equation

HRID 2214891 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[C:7]([CH:20]=[CH2:21])[C:6]=2[CH:22]=1.[OH-].[Na+]>C1COCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([F:13])([F:12])[F:14])[C:8]([C:15]([OH:17])=[O:16])=[C:7]([CH:20]=[CH2:21])[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21883512HCID 21883512, compound

Product 1

HCID 21883526HCID 21883526, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

The ester from Step 5 (0.300 g, 0.902 mmol) was dissolved in a THF-EtOH-H2O mixture (10 mL, 7:2:1) and treated with sodium hydroxide (0.360 mL, 0.902 mmol of a 2.5 N solution). This solution was stirred at room temperature for 18 hours. The solvent was evaporated and the residue was dissolved in water (10 mL). Diethyl ether (10 mL ) was added and the mixture acidified by the addition of concentrated HCl. The organic layer was separated, and the aqueous phase was extracted with diethyl ether (2×10 mL). The ether extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo yielding a yellow solid, which was recrystallized in diethyl ether-hexane to afford the title compound as a white solid (0.163 g, 59%): mp 143.0–145.0° C. 1H NMR (CDCl3/300 MHz 7.49 (d, 1H, J=2.6 Hz), 7.33–7.17 (m, 2H), 6.99 (d, 1H, J=8.5 Hz), 5.82–5.72 (m, 2H), 5.42 (d, 1H, J=17.9 Hz). ESHRMS m/z 303.00207 (M−H, Calc'd. 303.003582). Anal. Calc'd for C13H8ClF3O3 (1.10 wt % H2O): C, 50.69; H, 2.74; Cl, 11.51. Found: C, 50.57; H, 2.37; Cl, 11.75.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. additionDiethyl ether (10 mL ) was added
  4. additionthe mixture acidified by the addition of concentrated HCl
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was extracted with diethyl ether (2×10 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customyielding a yellow solid, which
  11. customwas recrystallized in diethyl ether-hexane

Sources & evidence

ORD record
ord-46784289620b4a8fb344eb0f6736a8b9
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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