反応 #1859590

反応方程式

p-toluene-sulfonic acid monohydrate

compound 22

4-([1,1′-Biphenyl]-2-yl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-ol

→

compound 23

収率 67.0%

7-([1,1′-Biphenyl]-2-yl)-2-((1-methylcyclohexyl)methyl)-1H-indene

収率 67.0%

溶媒

toluene

反応条件

後処理

1. 1
   温度was refluxed for 1 hour
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 was 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 (25-80 g) column
7. 7
   洗浄eluting with a gradient of 0 to 10% ethyl acetate in heptanes

実験手順

Mixture of p-toluene-sulfonic acid monohydrate (0.38 g, 2.0 mmol, 0.2 equiv), compound 22 (4.0 g crude, ˜9.88 mmol, 1.0 equiv) and toluene (100 mL) was refluxed for 1 hour. After cooling to room temperature, the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an AnaLogix (25-80 g) column, eluting with a gradient of 0 to 10% ethyl acetate in heptanes to give compound 23 (2.5 g, 67% yield for 2 steps) as a white solid.

出典