Propargyl alcohol → HCID 14271911, compound

A solution of ethyl 4-chloroacetoacetate (294 g) in tetrahydrofuran (200 ml) was added over 3hours to a stirred, ice-cooled suspension of sodium hydride (150 g of a 80% dispersion in mineral oil) in tetrahydrofuran (500 ml) at such a rate than the reaction temperature remained ≤20°. A solution of prop-2-ynol (100 g) in tetrahydrofuran (200 ml) was then added over 2 hours to the above mixture with stirring and ice-cooling at such a rate that the reaction temperature never exceeded +25°. The mixture was then stirred at room temperature for 16 hours, poured into 2 M HC1 (900 ml) and the layers separated. The organic layer was evaporated and the resulting red oil was separated in a separating funnel from the mineral oil. The red oil was taken up in dichloromethane and the resulting solution was washed several times with water, dried over Na2SO4 and evaporated to give the title compound (313 g) as a dark oil which was used directly in Preparation 8.

1. temperaturecooled
2. customremained ≤20°
3. temperatureice-cooling at such a rate that the reaction temperature never exceeded +25°
4. stirringThe mixture was then stirred at room temperature for 16 hours
5. additionpoured into 2 M HC1 (900 ml)
6. customthe layers separated
7. customThe organic layer was evaporated
8. customthe resulting red oil was separated in a separating funnel from the mineral oil
9. washthe resulting solution was washed several times with water
10. dry with materialdried over Na2SO4
11. customevaporated

ORD record

ord-2a6724c023864d70a2b0c3b02a826c2e

Source dataset

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04732985