Diethyl Ether → HCID 20431599, compound

100 ml of a 1N solution of methylmagnesium bromide in diethyl ether are placed under argon gasification and treated dropwise with a solution of 5.0 g of 3-[(2-hydroxyethyl)thio]propionic acid methyl ester (prepared according to Example 5) in 25 ml of diethyl ether so that a slight reflux results. After completion of the addition, the resulting mixture is stirred at room temperature for a further 16 hours. Subsequently, the excess Grignard reagent is destroyed by the cautious addition of saturated ammonium chloride solution to the mixture and the mixture is extracted three times with 100 ml of methylene chloride each time. The organic phases are dried over magnesium sulfate and concentrated. Low-pressure chromatography (0.4 bar) of the residue on silica gel with ethyl acetate and subsequent bulb-tube distillation (150° C./0.23-0.18 mm Hg) gives 2.25 g (46 percent) of 4-[(2-hydroxyethyl)thio]-2-methyl-2-butanol as a viscous, colorless oil; nD23 =1.5027.

1. temperaturea slight reflux
2. customresults
3. additionAfter completion of the addition
4. customSubsequently, the excess Grignard reagent is destroyed by the cautious addition of saturated ammonium chloride solution to the mixture
5. extractionthe mixture is extracted three times with 100 ml of methylene chloride each time
6. dry with materialThe organic phases are dried over magnesium sulfate
7. concentrationconcentrated
8. distillationLow-pressure chromatography (0.4 bar) of the residue on silica gel with ethyl acetate and subsequent bulb-tube distillation (150° C./0.23-0.18 mm Hg)

ORD record

ord-438892e6b48d42b684d3371070bbb9f9

Source dataset

uspto-grants-1985_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04493533