Tin tetrachloride → HCID 86702351, compound

HRID 2172542Notes

Reaction equation

[CH:1]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)SC1C=CC=CC=1.[Sn](Cl)(Cl)(Cl)Cl.[C:28]1([O:38][Si](C)(C)C)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH:29]=1>ClCCl>[C:17]1([S:16][CH:1]([S:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:29]2[CH2:30][CH2:31][C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:28]2=[O:38])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: -70 °C

Procedure

Under argon, 6.22 g (23.8 mmol) of triphenyl trithioorthoformate (1,1′,1″-(methanetriyltrisulphanediyl)dibenzene) are dissolved in anhydrous dichloromethane and cooled to −70° C. 23.8 ml (23.8 mmol) of tin(IV) tetrachloride solution (1 M in dichloromethane) and 5.73 g (26.3 mmol) of (3,4-dihydronaphthalen-1-yloxy)trimethylsilane are added in succession, and the mixture is stirred at −70° C. for 40 min. 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 5.80 g of 2-[bis(phenylsulphanyl)methyl]-3,4-dihydronaphthalen-1(2H)-one.

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-46e42e0298d24abe8a8d2274acb4a94f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09055743B2

Reaction notes

Loading…