Sodium Hydroxide → HCID 21883567, compound

HRID 2214881Notes

Reaction equation

HRID 2214881 reaction equation
C([O:3][C:4]([C:6]1[CH:7]([C:19]([F:22])([F:21])[F:20])[O:8][C:9]2[C:15]([CH:16]=[CH2:17])=[CH:14][C:13]([Cl:18])=[CH:12][C:10]=2[CH:11]=1)=[O:5])=C.[OH-].[Na+]>C1COCC1.C(O)C.O>[Cl:18][C:13]1[CH:14]=[C:15]([CH:16]=[CH2:17])[C:9]2[O:8][CH:7]([C:19]([F:21])([F:20])[F:22])[C:6]([C:4]([OH:5])=[O:3])=[CH:11][C:10]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21883586HCID 21883586, compound

Product 1

HCID 21883567HCID 21883567, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

The ester (Step 1) (0.350 g, 1.05 mmol) was dissolved in a solution of THF:ethanol:water (7:2:1; 10 mL), was treated with sodium hydroxide (0.46 mL, 1.05 mmol of a 2.5 N solution), and stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was dissolved in water (10 mL). Diethyl ether (10 mL) was added and the mixture acidified with concentrated HCl. The layers were separated, and the aqueous phase was extracted with diethyl ether (2×10 mL). The organic phases were combined, dried over MgSO4, filtered, and evaporated to yield a yellow solid, which was recrystallized in diethyl ether-hexane to afford the title compound as a yellow solid (0.288 g, 90%): mp 183.2–185.8° C. 1H NMR (CDCl3/300 MHz) 7.77 (s, 1H), 7.49 (d, 1H, J=2.2 Hz), 7.16 (d, 1H, J=2.4 Hz), 6.93 (dd, 1H, J=11.3, 17.7 Hz), 5.82 (d, 1H, J=17.7 Hz), 5.74 (q, 1H, J=6.9 Hz), 5.43 (d, 1H, J=11.1 Hz). FABLRMS m/z 303 (M−H). ESHRMS m/z 303.0014 (M−H, Calc'd. 303.003582). Anal. Calc'd. for C13H8ClF3O3+1.58% H2O: C, 50.44; H, 2.78. Found: C, 50.42; H, 2.65.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. additionDiethyl ether (10 mL) was added
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with diethyl ether (2×10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a yellow solid, which
  10. customwas recrystallized in diethyl ether-hexane

Sources & evidence

ORD record
ord-c915e2cfebc844389436e770fd71d57d
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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