反応 #2383788

反応方程式

hydrochloric acid

sodium

allyl alcohol

diallyl 3,3′-thiodipropionate

→

title compound

収率 42.3%

Allyl 4-hydroxy-5,6-dihydro-2H-thiopyrane-3-carboxylate

収率 42.3%

溶媒

water

diethyl ether

反応条件

後処理

1. 1
   workup.ADDITIONwas slowly added
2. 2
   その他The obtained reaction mixture
3. 3
   workup.STIRRINGThe mixture was stirred for another day at room temperature
4. 4
   workup.STIRRINGit was stirred until the whole
5. 5
   workup.DISSOLUTIONwas dissolved
6. 6
   その他The phases were separated
7. 7
   洗浄The obtained organic phase was washed with water (400 ml)
8. 8
   乾燥The organic phase was dried with magnesium sulfate
9. 9
   ろ過the drying agent was filtered off
10. 10
    その他the filtrate was evaporated
11. 11
    その他dried

実験手順

To a mixture of sodium sand (23 g; 1.0 mole) (Vogel's Textbook of Practical Organic Chemistry, Fourth Ed., Longman, London, 1978, p. 313) and anhydrous diethyl ether (3.4 1), allyl alcohol (65.8 ml) was slowly added. The obtained reaction mixture was stirred for two days at room temperature and then diallyl 3,3′-thiodipropionate (129.0 g; 0.5 mole) prepared according to the process disclosed in Example 1 was slowly added drop by drop. The mixture was stirred for another day at room temperature and then under ice cooling first absolute ethanol (10 ml) and then water (400 ml) and concentrated hydrochloric acid (455 ml) were added and it was stirred until the whole was dissolved. The phases were separated. The obtained organic phase was washed with water (400 ml), a 7% sodium hydrogencarbonate solution (3×400 ml) and once more with water (200 ml). The organic phase was dried with magnesium sulfate, the drying agent was filtered off, the filtrate was evaporated and dried. The title compound (42.4 g; 42%) was obtained as a crude product in the form of a yellowish oil.

出典