Thioguaiacol → HCID 21055320, compound

HRID 2215270Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[H-].[Na+].C1(C)C=CC(S([O:21][CH2:22][C@@H:23]([CH2:26][CH3:27])[CH2:24]O)(=O)=O)=CC=1>CN(C)C=O>[CH2:26]([C@H:23]([CH2:24][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:22][OH:21])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

0.47 ml (0.0038 mol) of 2-methoxythiophenol, in solution in 5 ml of dimethylformamide, is added dropwise to a round-bottomed flask, kept under an inert atmosphere, comprising 0.19 g (0.0047 mol) of sodium hydride in suspension in 10 ml of dimethylformamide cooled to 0° C. The mixture is reheated to ambient temperature and stirred for 1 hour, then 0.99 g (0.0038 mol) of 2-(S)-ethyl-3-hydroxypropyl p-toluene-sulfonate (XIXd-1), in solution in 10 ml of dimethyl-formamide, is added. After stirring at ambient temperature for 2 hours, the dimethylformamide is evaporated under high vacuum and the residue is taken up in dichloromethane. The organic phase is washed with water and with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=98:2). 0.87 g (0.0038 mol) of the title compound (XXd-1) is recovered in the form of an oil.

Workup

customis reheated to ambient temperature
stirringAfter stirring at ambient temperature for 2 hours
customthe dimethylformamide is evaporated under high vacuum
washThe organic phase is washed with water and with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=98:2)

Sources & evidence

ORD record: ord-100010604e0e4f21884f198001f55dc5
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109234B2

Reaction notes

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