Hydrochloric Acid → HCID 67593542, compound

HRID 865304Notes

Reaction equation

HRID 865304 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[CH2:15][S:14]1.Cl>O1CCCC1>[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)[CH2:13][S:14]1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 78150IsothiochromanoneHCID 10942334Sodium Methoxide

Product 1

HCID 67593542HCID 67593542, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl trifluoroacetate (3.67 g, 25.8 mmol) was dissolved in tetrahydrofuran (15 mL) and treated with 25% sodium methoxide (6.46 g, 29.9 mmol) followed by a solution of isothiochroman-4-one (4.15 g, 25.3 mmol) in tetrahydrofuran (15 mL). The reaction was stirred at room temperature for 70.8 hours and treated with 3N hydrochloric acid (10 mL). The organic layer was collected, washed with brine, dried over MgSO4, concentrated in vacuo, and passed through a column of silica gel eluting with 40% ethyl acetate/hexane to give a brown solid (5.40 g, 82%): 1H NMR (CDCl3) 300 MHz 15.30 (s, 1H) 7.99 (d, J=7.9 Hz, 1H) 7.54 (m, 1H) 7.43 (m, 1H) 7.23 (m, 1H) 3.81 (s, 3H).

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-e6e0cd90aa3d4851a22eb347ec73cd6b
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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