反応 #1751427

反応方程式

Diisopropylethylamine

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

hex-5-enal

→

title compound

収率 74.0%

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

収率 74.0%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

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
   その他The reaction was quenched by addition of half-saturated NH4Cl (30 mL)
4. 4
   抽出The mixture was extracted twice with dichloromethane
5. 5
   その他the organic phase was dried
6. 6
   その他evaporated
7. 7
   その他to provide a residue

実験手順

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.

出典