反応 #1859585

反応方程式

p-toluenesulfonic acid monohydrate

compound 14

4-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-ol

→

compound 15

収率 81.0%

7-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-1H-indene

収率 81.0%

溶媒

toluene

反応条件

後処理

1. 1
   温度was refluxed for 1 h
2. 2
   洗浄the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
3. 3
   乾燥The organic layer dried over sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The residue was purified on an AnaLogix (65-200 g) column
7. 7
   洗浄eluting with heptanes

実験手順

A mixture of p-toluenesulfonic acid monohydrate (0.88 g, 4.64 mmol, 0.2 equiv), compound 14 (10.0 g crude, 23.22 mmol, 1.0 equiv) and toluene (200 mL) was refluxed for 1 h. After cooling to room temperature, the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL). The organic layer dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an AnaLogix (65-200 g) column, eluting with heptanes to give compound 15 (7.8 g, 81% yield for 2 steps) as a white solid.

出典