Sodium hydride → (S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.CC1C=CC(S(O[CH2:23][C@H:24]2[O:26][CH2:25]2)(=O)=O)=CC=1.[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:23][C@@H:24]2[CH2:25][O:26]2)=[CH:7][CH:6]=1

Participants

Procedure

To a solution of 4-(2-methoxyethyl)phenol (42 mg, 0.275 mmol) and (2S)-(+)-glycidyl tosylate (57 mg, 0.25 mmol) in 2 mL of DMF was added 15 mg (0.625 mmol) of sodium hydride (60% in mineral oil). The resulting mixture was allowed to stir for 16 hours at room temperature. The solution was then extracted three times with ethyl acetate, and the organic phase was washed sequentially with sodium hydroxide, water and brine, dried over sodium sulfate, and concentrated in vacuo to provide the product which was used without further purification. m/z 208 [M+H]+.