Tin tetrachloride → HCID 178450088, compound

HRID 1423933Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([SH:12])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].[CH2:13]([O:15][C:16](=[O:28])[CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])[CH3:14].[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[CH2:13]([O:15][C:16]([C:17]1[C:18](=[O:19])[S:12][C:8]2[C:9]([C:23]=1[OH:24])=[CH:10][CH:11]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=2)=[O:28])[CH3:14]

Participants

Conditions

Temperature: 210 °C

Procedure

3-Butoxy-benzenethiol (1.2 g, 6.58 mmol) was dissolved in 2-ethoxycarbonyl-malonic acid diethyl ester (2.1 mL, 9.87 mmol). Tin tetrachloride (26 μL, 0.224 mmol) was added and the reaction was sealed and heated to 210° C. After 2 h, the reaction was cooled and directly subjected to silica gel chromatography (5%-50% ethyl acetate in hexanes) to provide 7-butoxy-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid ethyl ester (140 mg, 7%). MS ESI(−) m/e: 321.249 (M−1).

Workup

customthe reaction was sealed
temperaturethe reaction was cooled

Sources & evidence

ORD record: ord-be027ef90f19402a84b53f94b6f256a4
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927591B2

Reaction notes

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