반응 #617335

반응 방정식

(Z)-dec-4-en-1-ol

triethylamine

methane sulfonyl chloride

→

(Z)-dec-4-enyl methanesulfonate

수율 95.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   세척The solution was washed with saturated sodium bicarbonate (3×150 mL)
2. 2
   추출the combined aqueous washes were extracted with dichloromethane (150 mL)
3. 3
   건조The combined dichloromethane extracts were dried on magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo to dryness
6. 6
   여과The residue was filtered through a pad of silica (100% dichloromethane)

실험 절차

To a cooled solution (0° C.) of (Z)-dec-4-en-1-ol 9 (20 g, 128.0 mmol) and triethylamine (26.7 mL, 191.9 mmol) in anhydrous dichloromethane (200 mL) was slowly added methane sulfonyl chloride (14.9 mL, 191.9 mmol). The solution was stirred for 30 min at room temperature then diluted with dichloromethane (100 mL). The solution was washed with saturated sodium bicarbonate (3×150 mL) and then the combined aqueous washes were extracted with dichloromethane (150 mL). The combined dichloromethane extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was filtered through a pad of silica (100% dichloromethane) to afford (Z)-dec-4-enyl methanesulfonate 2 as a yellow oil (28.5 g, 95%). Rf 0.5 (100% CH2Cl2).

출처