反応 #80652

反応方程式

4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol

Compound 32

4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol

H2SO4

→

title compound

2,2,4,4-Tetramethyl-6-bromothiochroman

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 24 h
3. 3
   抽出The mixture was extracted with hexanes
4. 4
   洗浄washed successively with water, saturated NaHCO3, water again
5. 5
   乾燥saturated NaCl and then dried (MgSO4)
6. 6
   その他The solvent was removed in vacuo
7. 7
   その他the residue purified by flash chromatography (silica; hexanes)

実験手順

A mixture of 500 mg (1.49 mmol) of 4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol (Compound 32) and 8 ml of 20 percent aqueous H2SO4 was heated at reflux for 24 h. The mixture was extracted with hexanes, the organic extracts were combined and washed successively with water, saturated NaHCO3, water again, saturated NaCl and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; hexanes) to give the title compound as a colorless oil. PMR (CDCl3): & 1.35 (6H, s), 1.40 (6H, s), 1.93 (2H, s), 7.17 (1H, dd, J-8.4 Hz, 2.1 Hz), 7.23 (1H, d, J-8.4 Hz), 7.26 (1H, d, J-2.1 Hz). MS exact mass, m/e 16 284.0221 (calcd. for C13H17S Br, 284.0234).

出典