Sodium Hydroxide → 6-chloro-8-(5-chloro-1-pentynyl)-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylic acid

HRID 722324

Reaction equation

HRID 722324 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][Cl:26])[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.[OH-].[Na+]>C1COCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][Cl:26])[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21883733ethyl 6-chloro-8-(5-chloro-1-pentynyl)-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate

Product 1

HCID 218836996-chloro-8-(5-chloro-1-pentynyl)-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

The ester (Step 1) (0.500 g, 1.23 mmol) was dissolved in THF-ethanol-water(7:2:1; 10 mL). It was treated with sodium hydroxide (0.49 mL, 1.23 mmol of a 2.5 N solution), and 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 with concentrated HCl. The organic layer was separated, and the aqueous phase was extracted with diethyl ether (2×10 mL). The combined extracts were 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 (0.371 g, 80%): mp 154.4–156.4° C. 1H NMR (acetone-d6/300 MHz) 7.88 (s, 1H), 7.53 (d, 1H, J=2.4 Hz), 7.44 (d, 1H, J=2.4 Hz), 5.94 (q, 1H, J 7.1 Hz), 3.83 (t, 2H, J=6.5 Hz), 2.68 (t, 2H, J=6.8 Hz), 2.12–2.04 (m, 2H). ESLRMS m/z 377 (M−H). ESHRMS m/z 376.9930 (M−H, Calc'd. 376.9959). Anal. Calc'd. for C16H11Cl2F3O3+1.18% H2O: C, 50.08; H, 3.02; Cl, 18.48. Found: C, 50.11; H, 2.73; Cl, 18.28.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. additionDiethyl ether (10 mL) was added
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with diethyl ether (2×10 mL)
  6. dry with materialThe combined extracts were dried 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-f5ee12d2546648a3987b2d785027c708
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Linked notes

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