Tin tetrachloride → HCID 86702352, compound

HRID 2172545Notes

Reaction equation

[Sn](Cl)(Cl)(Cl)Cl.[C:6]1([S:12][CH:13]([S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]2[C:19]([O:20][Si](C(C)(C)C)(C)C)=[CH:18][CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[C:6]1([S:12][CH:13]([S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]2[CH2:15][CH2:16][CH2:17][CH:18]([CH:13]([S:12][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[S:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:19]2=[O:20])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

400 mg (1.18 mmol) of 1,1′,1″-(methanetriyltrisulphanediyl)tribenzene are dissolved in 25 ml of dichloromethane, and the mixture is cooled to −78° C. 1.41 ml (1.41 mmol) of tin(IV) tetrachloride solution (1 M in dichloromethane) and 520 mg (1.18 mmol) of (({6-[bis(phenylsulphanyl)methyl]-cyclohex-1-en-1-yl}oxy)(tert-butyl)dimethylsilane) are added in succession, and the mixture is stirred at −78° C. for 1 h. The reaction mixture is poured into ice-water and extracted with dichloromethane. After washing with water, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate) gives 341 mg of 2,6-bis[bis(phenylsulphanyl)methyl]cyclohexanone.

Workup

extractionextracted with dichloromethane
washAfter washing with water
dry with materialthe organic phase is dried over sodium sulphate
concentrationconcentrated under reduced pressure
customPurification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-4576b982887743b7a09be6ea4ed251d4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09055743B2

Reaction notes

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