反応 #2275726

反応方程式

1,4-dioxa-spiro[4.5]decan-8-ol

TsCl

→

title compound

Toluene-4-sulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester

溶媒

DCM

反応条件

後処理

1. 1
   その他The solution was partitioned between DCM and water
2. 2
   洗浄The organic layer was washed with brine
3. 3
   乾燥dried over anhydrous Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他to give white solid, which
7. 7
   その他was then purified by silica gel column on a CombiFlash® system (Teledyne Isco, Inc, Lincoln, Neb.) system

実験手順

A solution of 1,4-dioxa-spiro[4.5]decan-8-ol (prepared according to the procedure of Kayser, Margaret M.; Clouthier, Christopher M. Journal of Organic Chemistry (2006), 71(22), 8424-8430, 11 g, 70 mmol) in DCM (100 mL) was treated with TEA (11 mL, 77 mmol) followed by TsCl (Aldrich, 13.3 g, 70 mmol) slowly at 0° C. The reaction was warmed to room temperature over 2 hours. The solution was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give white solid, which was then purified by silica gel column on a CombiFlash® system (Teledyne Isco, Inc, Lincoln, Neb.) system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as white solid.

出典