Sodium Hydroxide → 7-(1,1-Dimethylethyl)-2-(pentafluoroethyl)-2H-1-benzopyran-3-carboxylic acid

HRID 2214879Notes

Reaction equation

HRID 2214879 reaction equation
[CH3:1][C:2]([C:5]1[CH:26]=[CH:25][C:8]2[CH:9]=[C:10]([C:20]([O:22]CC)=[O:21])[CH:11]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[O:12][C:7]=2[CH:6]=1)([CH3:4])[CH3:3].[OH-].[Na+]>C1COCC1.C(O)C>[CH3:4][C:2]([C:5]1[CH:26]=[CH:25][C:8]2[CH:9]=[C:10]([C:20]([OH:22])=[O:21])[CH:11]([C:13]([F:18])([F:19])[C:14]([F:17])([F:16])[F:15])[O:12][C:7]=2[CH:6]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21883731ethyl 7-(1,1-Dimethylethyl)-2-(pentafluoroethyl)-2H-1-benzopyran-3-carboxylate

Product 1

HCID 102693117-(1,1-Dimethylethyl)-2-(pentafluoroethyl)-2H-1-benzopyran-3-carboxylic acidYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 3 (1.58 g 4.20 mmol) was dissolved in THF (3 mL) and ethanol (3 mL), treated with 2.5 N sodium hydroxide (2 mL, 5 mmol), and stirred at room temperature for 23.3 hours. The reaction mixture was concentrated in vacuo, acidified with 3 N HCl yielding a suspension. The solid was collected by filtration and was recrystallized from ethanol-water to yield a yellow solid (0.76 g, 52%): mp 171.0–173.5° C. 1H NMR (acetone-d6/300 MHz) 7.93 (s, 1H), 7.39 (d, 1H, J=8.1 Hz), 7.18 (dd, 1H, J=8.1 Hz 1.8 Hz), 7.02 (s, 1H), 6.01 (dd, 1H, J=23.1 Hz 3.2 Hz), 1.32 (s, 9 H). FABLRMS m/z 351 (M+H). EIHRMS m/z 350.0945 (M+, Calc'd 350.0941). Anal. Calc'd for C16H15F5O3: C, 54.86; H, 4.32. Found: C, 54.88; H, 4.32.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe solid was collected by filtration
  3. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-b6a23f7cbd994650950e072eea7898d1
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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