Hydrochloric Acid → HCID 58934825, compound

HRID 855139Notes

Reaction equation

HRID 855139 reaction equation
[Cl:1][C:2]1[C:3]([F:22])=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19]CC)=[O:18])=[CH:5]2.[OH-].[Li+].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[C:3]([F:22])=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[O:8][CH:7]([C:13]([F:16])([F:14])[F:15])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58934938HCID 58934938, compound

Product 1

HCID 58934825HCID 58934825, compoundYield 72.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 359 mg (1.0 mmole) of ethyl 6,8-dichloro-5-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 7 mLs of THF and 2 mL of methanol was added a solution of 90 mg of lithium hydroxide monohydate in 1.0 mL of water. The mixture was heated to reflux for 60 min and allowed to cool to rt. After stirring overnight, the mixture was treated with 75 mL of 1N HCl and extracted three times with diethyl ether. The combined extracts were concd and purified by reverse phase chromatography to afford 240 mg of an impure white solid. Recrystallization from acetonitrile afforded 51 mg (15%) of a white, crystalline solid: 1H NMR (d6-acetone/400 MHz) 6.08 (q, 1H, J=7.0 Hz), 7.74 (d, 1H, J=7.7 Hz), 7.94 (s, 1H); 19F NMR (d6-acetone/400 MHz) −122.1 (d, 1F, J=7.7 Hz), −79.4 (d, 3F, J=6.8 Hz); MS (ES+) 331 (M+1, 100), 333 (M+3, 57); MS (ES−) 329 (M−1, 100), 331 (79); HRMS (ES−) m/z calcd for (C11H4C12F4O3) 328.9401, found 328.9357.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 60 min
  3. extractionextracted three times with diethyl ether
  4. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-0beddd5d41c441b8869a1d9172ed1250
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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