Sodium Hydroxide → 6-Methyl-2-(trifluoromethyl)-2H-1-benzothiopyran-3-carboxylic acid

HRID 393323Notes

Reaction equation

HRID 393323 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S: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>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH:9]([C:11]([F:13])([F:14])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21883614ethyl 6-methyl-2-(trifluoromethyl)-2H-1-benzothiopyran-3-carboxylate

Product 1

HCID 218835306-Methyl-2-(trifluoromethyl)-2H-1-benzothiopyran-3-carboxylic acidYield 28.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 2 (0.55 g 1.8 mmol) was dissolved in THF (1.5 mL) and ethanol (1.5 mL), treated with 2.5 N sodium hydroxide (1.5 mL, 3.8 mmol), and stirred at room temperature for 88 hours. The reaction mixture was concentrated in vacuo, acidified with 3 N HCl, filtered, and recrystallized from diethyl ether/petroleum ether to yield the title compound as a yellow solid (0.14 g, 28%): mp 180.8-184.2° C. 1H NMR (acetone-d6/300 MHz) 7.95 (s, 1H), 7.42 (s, 1H), 7.31 (d, 1H, J=8.1 Hz), 7.25 (d, 1H, J=8.1 Hz), 4.94 (q, 1H, J=8.7 Hz), 2.34 (s, 3H). FABLRMS m/z 281 (M+Li). EIHRMS m/z 274.0250 (M+, Calc'd 274.0275). Anal. Calc'd for C12H9F3O2S: C, 52.55; H, 3.31. Found: C, 52.54; H, 3.35.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered
  3. customrecrystallized from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-3d25dd2f4eb441be86eaf7198d3af3e3
Source dataset
uspto-grants-2004_10
Patent number
US06806288B1

Reaction notes

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