Hydrochloric Acid → HCID 54244781, compound

HRID 1379145Notes

Reaction equation

HRID 1379145 reaction equation
[CH3:1][O:2][C:3]1[C:12]([F:13])=[C:11]2[C:6]([C:7](=[O:14])[CH2:8][O:9][CH2:10]2)=[CH:5][CH:4]=1.[F:15][C:16]([F:23])([F:22])[C:17](OCC)=[O:18].C[O-].[Na+].CO.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[C:12]([F:13])=[C:11]2[C:6]([C:7](=[O:14])[CH:8]([C:17](=[O:18])[C:16]([F:23])([F:22])[F:15])[O:9][CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 54108731HCID 54108731, compound

Product 1

HCID 54244781HCID 54244781, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-methoxy-8-fluoro-isochroman-4-one from Step 2 (370 mg, 1.76 mmol) and ethyl trifluoroacetate (290 mg, 2.04 mmol) in 8 mL of anhydrous tetrahydrofuran was treated with a solution of 25% sodium methoxide in methanol (570 mg, 2.64 mmol). The solution was stirred at room temperature for 16 hours, treated with excess 3N hydrochloric acid, and extracted with ether. The ethereal extract was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford 450 mg (88%) of pure 7-methoxy-8-fluoro-3-(trifluoroacetyl)isochroman-4-one which was used directly in the next step without further purification.

Workup

  1. extractionextracted with ether
  2. extractionThe ethereal extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46c6fd1764ff42f8831a55f48e7524b5
Source dataset
uspto-grants-1997_09
Patent number
US05670532

Reaction notes

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