反応 #7998

反応方程式

2-(2-methoxy-5-methyl-6-oxo-6,7,8,9-tetrahydro-8aH-fluoren-8a-yl)ethyl methanesulfonate

sodium iodide

→

9a-(2-iodoethyl)-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

収率 64.0%

溶媒

acetone

acetone

反応条件

後処理

1. 1
   温度After cooling
2. 2
   ろ過filtered through a 0.45 Fm Acrodisc
3. 3
   ろ過filter
4. 4
   その他The filtrate was evaporated under vacuum
5. 5
   ろ過the residue in CH2Cl2 (3 mL) was re-filtered
6. 6
   その他The filtrate was purified by chromatography on a Biotage Flash 12M KP-Sil column (12 mm×15 cm) which
7. 7
   洗浄was eluted with 4:1 hexanes-EtOAc
8. 8
   その他collecting 6 mL fractions every 30 seconds

実験手順

A solution of 2-(2-methoxy-5-methyl-6-oxo-6,7,8,9-tetrahydro-8aH-fluoren-8a-yl)ethyl methanesulfonate (49.7 mg, 0.142 mmol) in acetone (2.0 mL) was treated with sodium iodide (85 mg, 0.57 mmol) and the resulting mixture was stirred and heated in an oil bath at 60° C. for 16 hours. After cooling, the mixture was diluted with acetone (2 mL) and filtered through a 0.45 Fm Acrodisc filter. The filtrate was evaporated under vacuum and the residue in CH2Cl2 (3 mL) was re-filtered. The filtrate was purified by chromatography on a Biotage Flash 12M KP-Sil column (12 mm×15 cm) which was eluted with 4:1 hexanes-EtOAc, collecting 6 mL fractions every 30 seconds. Fractions 9-11 gave 9a-(2-iodoethyl)-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (34.5 mg, 64% yield) as an oil.

出典