反応 #1973982

反応方程式

hydrochloric acid

5-bromo-2,3-dihydro-1H-inden-1-one

1,3-dithiane

n-butyllithium

→

oil

収率 100.0%

5-bromo-1-(1,3-dithian-2-yl)-2,3-dihydro-1H-inden-1-ol

収率 100.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度maintaining the temperature between −9° C. and 2° C
2. 2
   workup.WAITto set in the refrigerator at 2-8° C. for 18 h
3. 3
   濃縮The solution was concentrated in vacuo
4. 4
   その他to afford a maroon oil, which
5. 5
   抽出extracted with ether
6. 6
   抽出The ether layer was extracted with saturated sodium chloride solution
7. 7
   乾燥dried (Na2SO4)
8. 8
   濃縮concentrated in vacuo

実験手順

A solution of 1,3-dithiane (11.96 g, 99 mmol) in anhydrous tetrahydrofuran (100 mL) at −30° C. was treated dropwise over 10 min with n-butyllithium (2.5M in hexanes, 38.4 mL, 96 mmol) followed by stirring at −15° C. for 2 h. The solution was then treated with a solution of 5-bromo-2,3-dihydro-1H-inden-1-one (15 g, 71.1 mmol) in anhydrous tetrahydrofuran (250 mL) over 1 h, maintaining the temperature between −9° C. and 2° C. The mixture was then allowed to set in the refrigerator at 2-8° C. for 18 h. The solution was concentrated in vacuo to afford a maroon oil, which was treated with 1 N hydrochloric acid solution and extracted with ether. The ether layer was extracted with saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo to afford an amber oil (23.55 g).

出典