反应 #362580

反应方程式

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol

compound

3,6-Dioxabicyclo[3.1.0]hexane

→

trans-4-[[3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl]thio]tetrahydro-3-furanol

反应条件

后处理

1. 1
   其他a degassed (Argon) solution of 50% sodium hydroxide (5 ml) and isopropyl alcohol (50 ml)
2. 2
   温度The reaction was heated
3. 3
   温度to reflux for 24 hours
4. 4
   workup.ADDITIONpoured into water (125 ml)
5. 5
   萃取extracted 3 times with 100 ml of diethyl ether
6. 6
   干燥The combined diethyl ether extracts were dried over anhydrous magnesium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated to an oily solid in a rotary evaporator
9. 9
   其他The product was purified by silica gel chromatography
10. 10
    其他recrystallized from hexane (m.p. ca. 104° C.)

实验过程

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (1.85 g, 0.0078 mole) and the compound of Example 1 (0.64 g, 0.0074 mole) were added to a degassed (Argon) solution of 50% sodium hydroxide (5 ml) and isopropyl alcohol (50 ml). The reaction was heated to reflux for 24 hours. The reaction was cooled to room temperature and poured into water (125 ml). The solution was made acidic with 1N hydrochloric acid and extracted 3 times with 100 ml of diethyl ether. The combined diethyl ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to an oily solid in a rotary evaporator. The product was purified by silica gel chromatography and recrystallized from hexane (m.p. ca. 104° C.). The structure was supported by NMR and infrared spectroscopy and elemental analysis.

来源