Hydrochloric Acid → HCID 21281083, compound

HRID 414497Notes

Reaction equation

[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH2:3][OH:4].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.Cl>N1C=CC=CC=1>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([O:4][CH2:3][C:2]([CH3:22])([CH3:1])[CH2:5][O:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:9]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propan-1-ol (5 g), p-toluenesulphonyl chloride (3.75 g) and pyridine (10 cm3) was stirred at the ambient temperature (ca. 20° C.) for 24 hours. The mixture was poured into dilute aqueous hydrochloric acid solution and hhe aqueous mixture extracted with ethyl acetate (3×250 cm3). The combined organic layers were washed with brine, then dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave a dark oil (4 g) which was purified by column chromatography on a silica gel support, eluting with petroleum ether (boiling range (60°-80° C.) containing 20% by volume ethyl acetate, to give the title compound (3.9 g) as a yellow oil.

Workup

extractionextracted with ethyl acetate (3×250 cm3)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous magnesium sulphate
customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-7d29af91242348b4abdcb3534ac798a2
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792563

Reaction notes

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