Hydrochloric Acid → HCID 67594636, compound

HRID 865292Notes

Reaction equation

HRID 865292 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[O:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH2:14]1.Cl>CCOCC>[F:9][C:2]([F:1])([F:8])[C:3]([CH:14]1[C:15](=[O:22])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:13]1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 23556CoumaranoneHCID 10942334Sodium Methoxide

Product 1

HCID 67594636HCID 67594636, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl trifluoroacetate (1.90 g, 14 mmol) was dissolved in ether (15 mL) and treated with sodium methoxide (25%) (3.67 g, 17 mmol). To the stirred solution was added 3-coumaranone (1.50 g, 11 mmol). The reaction was stirred at room temperature overnight (19 hours) and treated with 3N HCl (8 mL). The organic layer was collected, washed with brine, dried over MgSO4, and concentrated in vacuo to give a reddish brown solid (2.19 g, 85%): mp 108°-111° C.; 1H NMR (CDCl3) 300 MHz 7.84 (d, J=8.1 Hz, 1H) 7.66 (m, 1H) 7.52 (d, J=8.7 Hz, 1H) 7.37 (m, 1H). Mass spectrum: M+H=231.

Workup

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d5a63d5ad2d46fba0efc4db825c2b14
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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