Sodium Hydroxide → 7-(3-(3-Trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylic Acid

HRID 51076Notes

Reaction equation

HRID 51076 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:29]=[C:28]4[C:23]([CH2:24][CH2:25][C:26]([CH2:35][CH3:36])([C:30]([O:32]CC)=[O:31])[O:27]4)=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][N:4]=1.[OH-].[Na+]>C(O)(C)C>[F:38][C:2]([F:1])([F:37])[C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:29]=[C:28]4[C:23]([CH2:24][CH2:25][C:26]([CH2:35][CH3:36])([C:30]([OH:32])=[O:31])[O:27]4)=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69898123Ethyl 7-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylate

Product 1

HCID 101857347-(3-(3-Trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylic AcidYield 100.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Ethyl 7-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylate (49 mg, 0.092 mmol) was dissolved in isopropanol 2 ml and 2N NaOH aq. 1 ml and was stirred at 70° C. overnight. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and 2N HCl aq. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound 47 mg as a pale yellow oil (quant.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and 2N HCl aq. The organic layer
  3. customwas separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf7fc24e18f848318131251554373777
Source dataset
uspto-grants-2004_03
Patent number
US06713508B2

Reaction notes

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