Tin tetrachloride → HCID 178470016, compound

HRID 1423903Notes

Reaction equation

HRID 1423903 reaction equation
Cl[Sn](Cl)(Cl)Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([SH:14])[CH:11]=[CH:12][CH:13]=1.[CH2:15]([O:17][C:18](=[O:30])[CH:19]([C:25](OCC)=[O:26])[C:20](OCC)=[O:21])[CH3:16]>CCOC(C)=O.C(Cl)Cl>[CH2:15]([O:17][C:18]([C:19]1[C:20](=[O:21])[S:14][C:10]2[C:11]([C:25]=1[OH:26])=[CH:12][CH:13]=[C:8]([O:7][CH3:6])[CH:9]=2)=[O:30])[CH3:16]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 80471Triethyl methanetricarboxylateHCID 849893-Methoxybenzenethiol

Product 1

HCID 178470016HCID 178470016, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
210 °C

Procedure

SnCl4 was added to a neat mixture of 3-methoxy-benzenethiol (0.91 g, 6.5 mmol) and 2-ethoxycarbonyl-malonic acid diethyl ester (2.27 g, 9.77 mmol) in a 20-mL open vial. The reaction mixture was heated in a 210° C. oil bath for 2.5 h. After cooling, the reaction mixture was subjected to silica gel chromatography (3%-50% EtOAc/CH2Cl2) to provide 4-hydroxy-7-methoxy-2-oxo-2H-thiochromene-3-carboxylic acid ethyl ester (100 mg). MS ESI(+) m/e: 281.10 (M+1).

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-614112b392c941fa8feacc384c848817
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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