Reaktion #2466682

Reaktionsgleichung

tetrakis-(bromomethyl)methane

3-hydroxymethyl-3-methyloxetane

hydrogen

Sodium hydride

→

tetrakis-[(3-methyl-3-oxetanyl)methoxymethyl]methane

Ausbeute 21.3%

Lösungsmittel

DMF

DMF

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea beige solid precipitated
2. 2
   Sonstigehad been consumed
3. 3
   workup.ADDITIONThe mixture was poured into 500 mL of water
4. 4
   Extraktionextracted with three portions of 200 mL of methylene chloride
5. 5
   WaschenThe combined organic extracts were washed with 3 portions of 200 mL of water
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto give an oil
9. 9
   TemperaturThe oil was cooled to -15° C. for 24 h
10. 10
    Sonstigethe solid that formed
11. 11
    Sonstigewas triturated with ether
12. 12
    Filtrationfiltered
13. 13
    Sonstigerecrystallized from ethanol

Vorschrift

Sodium hydride (50% dispersion in mineral oil, 16.10 g. 0.33 mol) was washed twice with hexanes and was suspended in 500 mL of DMF. Then, 3-hydroxymethyl-3-methyloxetane (34.2 g, 0.33 mol) was added dropwise over 45 min while hydrogen gas was evolved and a beige solid precipitated. The mixture was stirred for 30 min and a solution of tetrakis-(bromomethyl)methane (25.0 g, 0.0645 mol) in 250 mL of DMF was added. The mixture was heated to 100° C. for 64 h when 1H NMR analysis of an aliquot showed that the starting halide had been consumed. The mixture was poured into 500 mL of water and extracted with three portions of 200 mL of methylene chloride. The combined organic extracts were washed with 3 portions of 200 mL of water, dried over magnesium sulfate, and evaporated to give an oil. The oil was cooled to -15° C. for 24 h, and the solid that formed was triturated with ether, filtered, and recrystallized from ethanol to give 6.15 g (21.3%) of tetrakis-[(3-methyl-3-oxetanyl)methoxymethyl]methane, mp 108.5°-109.5° C.

Quelle