Reaktion #335251

Reaktionsgleichung

lithium hydride

1-propanethiol

[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy-alpha-ethyl-benzeneacetic acid, methyl ester

→

title compound

Ausbeute 75.4%

[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy-alpha-ethyl-benzeneacetic acid

Ausbeute 75.4%

Lösungsmittel

hexamethylphosphoramide

hexamethylphosphoramide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStir for 20 hours
2. 2
   ExtraktionExtract into ethyl ether (4×300 mL)
3. 3
   Waschenwash with water (500 mL)
4. 4
   Trocknendry (MgSO4)
5. 5
   SonstigeEvaporate the solvent in vacuo
6. 6
   Sonstigepurify by flash chromatography (5→10→20% isopropanol/hexane)

Vorschrift

Suspend lithium hydride (1.01 g, 126.4 mmol) in hexamethylphosphoramide (50 mL) and treat with 1-propanethiol (11.5 mL, 126.4 mmol). Stir for 1.5 hours and add to a solution of 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy-alpha-ethyl-benzeneacetic acid, methyl ester (5.57 g, 18.06 mmol) in hexamethylphosphoramide (50 mL) under a nitrogen atmosphere. Stir for 20 hours and pour into ice cold 5% hydrochloric acid (500 mL). Extract into ethyl ether (4×300 mL), wash with water (500 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (5→10→20% isopropanol/hexane) to give the title compound (4.01 g).

Quelle