Hydrochloric Acid → HCID 53937392, compound

HRID 865300Notes

Reaction equation

HRID 865300 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[S:21][CH2:20][CH2:19][C:18]2=[O:27].Cl>O1CCCC1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[S:21][CH2:20][CH:19]([C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[C:18]2=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 849531HCID 849531, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 53937392HCID 53937392, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl trifluoroacetate (0.84 g, 5.9 mmol) was dissolved in tetrahydrofuran (20 mL), and treated with 25% sodium methoxide (1.68 g, 7.8 mmol). To the stirred solution was added 6,7-dimethoxythiochroman-4-one from Step 2 (1.12 g, 5.0 mmol). The reaction was stirred at room temperature for 87.5 hours, treated with 3N HCl (25 mL) and filtered to give an orange solid (1.04 g, 65%): mp 148°-151° C.; 1H NMR (CDCl3) 300 MHz 16.05 (s, 1H), 7.48 (s, 1H) 6.78 (s, 1H) 3.94 (s, 3H) 3.92 (s, 3H) 3.83 (s, 2H); 19F NMR (CDCl3) 300 MHz -71.06 (s). Mass spectrum: M+H=321.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-efd3396394834d57bdd981272d525313
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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