Reacción #1751427

Ecuación de reacción

Diisopropylethylamine

(R)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone

hex-5-enal

→

title compound

Rendimiento 74.0%

(R)-3-Hydroxy-1-((R)-4-isopropyl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

Rendimiento 74.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 1 h at −78° C
2. 2
   workup.STIRRINGthe mixture was stirred for 2 h at −78° C
3. 3
   OtroThe reaction was quenched by addition of half-saturated NH4Cl (30 mL)
4. 4
   ExtracciónThe mixture was extracted twice with dichloromethane
5. 5
   Otrothe organic phase was dried
6. 6
   Otroevaporated
7. 7
   Otroto provide a residue

Procedimiento

A solution of (R)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone (11.8 g, 58.1 mmol) in dichloromethane (380 mL) under an atmosphere of nitrogen was cooled to −78° C., titanium tetrachloride (6.37 mL, 58.1 mmol) was added, and the mixture was stirred for 10 min. Diisopropylethylamine (10.12 mL, 58.1 mmol) was added, and the mixture was stirred for 1 h at −78° C. A 1 M solution of hex-5-enal (58.1 mL, 58.1 mmol) in dichloromethane was added, and the mixture was stirred for 2 h at −78° C. The reaction was quenched by addition of half-saturated NH4Cl (30 mL) and warmed to room temperature. The mixture was extracted twice with dichloromethane, and the organic phase was dried and evaporated to provide a residue. Chromatography on silica gel afforded the title compound (12.92 g, 74%). This procedure has also been carried out using the (R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)ethanone auxiliary, with a similar result.

Fuente