반응 #935906

반응 방정식

hydrogen

sodium hydride

n-decyl-dimethyl-(3-iodopropyl)-silane

dimethyl malonate

→

title product

Methyl-2-methoxycarbonyl-6,6-dimethyl-6-sila-n-hexadecanoate

용매

—

petroleum ether

water

acetic acid

dimethylformamide

—

petroleum ether

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   세척which is washed free of the oil
3. 3
   기타is at 0° to 10°
4. 4
   workup.STIRRINGThe reaction mixture is then stirred in a bath at 55° for 2 hrs
5. 5
   기타The organic layer is separated
6. 6
   세척washed thrice with water
7. 7
   기타dried
8. 8
   농축concentrated
9. 9
   기타to obtain the crude title product of this step as an oily residue, which
10. 10
    workup.DISTILLATIONis distilled through a Vigreux column

실험 절차

To a reaction vessel system filled with nitrogen, 964 mg (24.5 mmole) of 61.1% sodium hydride in mineral oil is added, which is washed free of the oil by employing 3 portions of petroleum ether/hexane (1:1). The thus-washed sodium hydride is then suspended in 20 ml of fresh hexane and added in several portions to 8.1 g (22.0 mmoles) of n-decyl-dimethyl-(3-iodopropyl)-silane plus 3.6 g (27.3 mmole) of dimethyl malonate in 25 ml of dry dimethylformamide plus 25 ml of dry petroleum ether, with stirring and cooling at such a rate that hydrogen gas evolution is controlled, and the temperature is at 0° to 10° (new solids form). The reaction mixture is then stirred in a bath at 55° for 2 hrs. and then at 65° for 1 hr. After cooling to room temperature, 2 ml of acetic acid (85%) is added, followed by an excess of water and petroleum ether. The organic layer is separated, washed thrice with water, dried and then concentrated to obtain the crude title product of this step as an oily residue, which is distilled through a Vigreux column to obtain refined title product of this step at 135°-139° at 0.105 mm Hg.

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