Sodium Acetate → HCID 75600536, compound

HRID 2281028Notes

Reaction equation

HRID 2281028 reaction equation
[CH2:1]([N:3]1[C:7](=[S:8])[CH2:6][O:5][C:4]1=[S:9])[CH3:2].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[O:22][C:21]([CH:23]=O)=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[C:7](=[S:8])[C:6](=[CH:23][C:21]2[O:22][C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][CH3:10])=[CH:19][CH:20]=2)[O:5][C:4]1=[S:9])[CH3:2]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 46749915-(2-Methoxyphenyl)-2-furancarboxaldehydeHCID 86676053HCID 86676053, compound

Product 1

HCID 75600536HCID 75600536, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 3-ethyloxazolidine-2,4-dithione 6 (79 mg, 0.49 mmol), 5-(2-methoxyphenyl)-2-furaldehyde 9 (99 mg, 0.49 mmol) and sodium acetate (201 mg, 2.45 mmol) was added acetic acid (5 mL). As more of the desired product was formed, the reaction mixture color turned to a very red solution. The reaction mixture was refluxed overnight, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. Flash column chromatography afforded the desired product 2 (M103) in 95% yield (160 mg, purple solid).

Sources & evidence

ORD record
ord-bf9f6bc7873a4108a34da8f8d5a4511c
Source dataset
uspto-grants-2015_09
Patent number
US09139575B2

Reaction notes

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