Hydrochloric Acid → HCID 86599504, compound

HRID 855128Notes

Reaction equation

HRID 855128 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([O:28][C:29]([F:32])([F:31])[F:30])[CH:12]=[C:13]3[C:18]=2[O:17][CH:16]([C:19]([F:22])([F:21])[F:20])[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:14]3)O1.[OH:34]O.[OH-].[Na+].Cl>C1COCC1.[Cl-].[Na+].O>[OH:34][C:9]1[CH:10]=[C:11]([O:28][C:29]([F:30])([F:31])[F:32])[CH:12]=[C:13]2[C:18]=1[O:17][CH:16]([C:19]([F:21])([F:20])[F:22])[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:14]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86599505HCID 86599505, compound

Product 1

HCID 86599504HCID 86599504, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Step 1 (600 mg, 1.24 mmole) in THF (20. mL) was added 30% H2O2 (192uL, 1.86 mmole) and aqueous NaOH (500 uL-2.5 N, 1.25 mmole) at 0° C. and the mixture was allowed to warm to room temperature. After stirring for 3.5 hrs, the mixture was acidified with 1N HCl, brine (50 mL) was added and the mixture was extracted with EtOAc (200 mL). The extract was dried over MgSO4, filtered and concentrated in vacuo to give a yellow crystalline solid. The crude product was purified by silica chromatography (0%-25% EtOAc in hexanes) to give 422 mg (91% yield) of the product as an off-white solid: EIHRMS m/z 372.0421 (M+, C14H10F6O5, Calc'd 372.0432).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc (200 mL)
  3. dry with materialThe extract was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow crystalline solid
  7. customThe crude product was purified by silica chromatography (0%-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-36302b02a43e46978e12ca5ab98e5757
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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