Ethyl trifluoroacetate → HCID 6917119, compound

HRID 865290Notes

Reaction equation

HRID 865290 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[O:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[CH2:15][CH2:14]1>CCOCC>[F:9][C:2]([F:1])([F:8])[C:3]([CH:15]1[C:16](=[O:23])[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:13][CH2:14]1)=[O:5]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 68110ChromanoneHCID 10942334Sodium Methoxide

Product 1

HCID 6917119HCID 6917119, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl trifluoroacetate (9.78 g, 68 mmol) was placed in a 250 mL round bottom flask, and dissolved in ether (50 mL). To the stirred solution was added 25% sodium methoxide (15.11 g, 70 mmol), followed by 4-chromanone (10.07 g, 68 mmol) dissolved in ether (25 mL). The reaction was stirred at room temperature overnight (18.3 hours), poured into a separatory funnel and washed with 3N hydrochloric acid (20 mL) and with brine (20 mL), dried over MgSO4, concentrated in vacuo, and recrystallized from ether/hexane to give a yellow solid (10.72 g, 65%): mp 81°-83° C.; 1H NMR (CDCl3) 300 MHz 16.04 (br s, 1H) 7.84 (d, J=7.9 Hz, 1H) 7.51 (m, 1H) 7.09 (m, 1H) 6.98 (d, J=8.5 Hz, 1H) 5.08 (s, 2H); 19F NMR (CDCl3) 300 MHz: -72.56 (s). Mass spectrum: M+=244.

Workup

  1. additionpoured into a separatory funnel
  2. washwashed with 3N hydrochloric acid (20 mL) and with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-29a345f1b30840a79d169076e4d2f0a5
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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