Sodium Hydroxide → HCID 23687344, compound

HRID 855166Notes

Reaction equation

HRID 855166 reaction equation
[CH3:1][C:2]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:3]=1[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([OH:21])=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][CH:6]=1.[OH-].[Na+:28]>C(O)C.C1COCC1.O>[CH3:1][C:2]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:3]=1[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([O-:21])=[O:20])[CH:11]([C:15]([F:17])([F:18])[F:16])[O:12]2)=[CH:7][CH:6]=1.[Na+:28]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 11200014HCID 11200014, compound

Product 1

HCID 23687344HCID 23687344, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 116 mg of 7-(2,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid (0.318 mmol) in 4 mL of ethanol and 2 mL of THF was added 3.15 mL (0.318 mmol) of a 0.1008 N NaOH solution in water. The resulting solution was stirred at room temperature for 15 min. The volatiles were removed. To the solution was added 2 mL of water and the resulting suspension was cooled at −78° C. and solidified then put on high vacuum for lyophilization. The ivory solid was registered as PHA-807535A: 1H NMR (CD3OD/400 MHz) 2.08 (s, 3H), 2.28 (s, 3H), 5.77 (q, 1H, J=7.6 Hz), 6.31 (d, 1H, J=2.0 Hz), 6.41 (dd, 1H, J=2.4 Hz, 8.4 Hz), 6.78 (s, 1H), 6.94 (d, 1H, J=8.0 Hz), 7.11-7.15 (m, 2H), 7.38 (s, 1H); MS (ES+) 365 (M+l, 100); LC-MS purity 100% at 3.575 min. (UV), 100% ELSD.

Workup

  1. customThe volatiles were removed
  2. additionTo the solution was added 2 mL of water
  3. temperaturethe resulting suspension was cooled at −78° C.
  4. waitLC-MS purity 100% at 3.575 min. (UV), 100% ELSD

Sources & evidence

ORD record
ord-37985c54fd9d4118859584a96d5af89f
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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