反応 #992

反応方程式

(S)-1-amino-2-propanol

potassium tertiary butoxide

2-Chloropyridine

→

title compound

収率 84.4%

(S)-N-(2-pyridyl)-1-amino-2-propanol

収率 84.4%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他After the exothermic reaction
2. 2
   温度the reaction was heated
3. 3
   温度under reflux overnight
4. 4
   ろ過filtered
5. 5
   その他to remove the potassium chloride
6. 6
   その他evaporated to an oil
7. 7
   workup.DISSOLUTIONThe crude oil was dissolved in xylene (500 ml)
8. 8
   workup.ADDITIONtoluene-p-sulphonic acid (2 g) added
9. 9
   温度heated overnight
10. 10
    温度under reflux under argon
11. 11
    抽出the mixture was extracted with 2M hydrochloric acid
12. 12
    抽出extracted into ethyl acetate
13. 13
    乾燥The ethyl acetate extracts were dried (MgSO4)
14. 14
    その他after removal of the acetic acid the product
15. 15
    workup.DISTILLATIONwas distilled

実験手順

(S)-1-amino-2-propanol (43 g, 0.57M) was added to a stirred solution of potassium tertiary butoxide (64.2 g, 0.66M) in tetrahydrofuran (500 ml). 2-Chloropyridine (65.1 g 0.66M) was then added dropwise. After the exothermic reaction had subsided, the reaction was heated under reflux overnight, filtered to remove the potassium chloride and evaporated to an oil. The crude oil was dissolved in xylene (500 ml) and toluene-p-sulphonic acid (2 g) added and heated overnight under reflux under argon. After cooling to room temperature, the mixture was extracted with 2M hydrochloric acid. The acid extracts were basified with 2M sodium hydroxide and extracted into ethyl acetate. The ethyl acetate extracts were dried (MgSO4) and after removal of the acetic acid the product was distilled affording 73.5 g of the title compound, bp 100°-110° C. at 0.2 mbar.

出典