Hydrochloric Acid → HCID 15406808, compound

HRID 865291Notes

Reaction equation

HRID 865291 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[F:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[O:20][CH2:19][CH2:18][C:17]2=[O:24].Cl>CCOCC>[F:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[O:20][CH2:19][CH:18]([C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[C:17]2=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 27332626-fluoro-2,3-dihydro-4H-1-benzopyran-4-oneHCID 10942334Sodium Methoxide

Product 1

HCID 15406808HCID 15406808, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl trifluoroacetate (4.33 g, 30 mmol) was dissolved in ether (25 mL) and treated with sodium methoxide (25%, 7.08 g, 33 mmol). To the stirred solution was added 6-fluoro-4-chromanone (4.92 g, 30 mmol) and additional ether (10 mL). The reaction was stirred at room temperature overnight (19.0 hours) and treated with 3N hydrochloric acid (15 mL). The organic layer was collected, washed with brine, dried over MgSO4, concentrated in vacuo and recrystallized from ether/hexane to give a yellow solid (3.98 g, 51%): mp 107°-112° C.; 1H NMR (CDCl3) 300 MHz 14.95 (s, 1H) 7.52 (dd, 1H) 7.23 (m, 1H) 6.97 (m, 1H) 5.07 (s, 2H); 19F NMR (CDCl3) 300 MHz -72.60 (s), -119.93 (m). Mass spectrum: M+=262.

Workup

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-9f00b02e4d894556b004f535e3623184
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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