Реакция #2050056

Уравнение реакции

ethanol

Sodium hydride

(3-methyl-1-oxa-4-aza-spiro[4.5]dec-3-yl)-methanol

Propargyl bromide

→

3-methyl-3-prop-2-ynyloxymethyl-1-oxa-4-aza-spiro[4.5]decane

Растворители

THF

diethyl ether

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 2.5 h
2. 2
   Фильтрацияthe mixture was filtered
3. 3
   КонцентрированиеThe filtrate was concentrated in vacuo
4. 4
   Другоеto providing a crude residue which
5. 5
   Другоеwas purified by column chromatography (hexane/ethyl acetate 1:1)

Методика

Sodium hydride (55% in dispersion in oil) (0.636 g) was added portion wise to a solution of (3-methyl-1-oxa-4-aza-spiro[4.5]dec-3-yl)-methanol (2.0 g) in dry THF (30 ml) at 0° C. The reaction mixture was stirred at room temperature for 1 h. Propargyl bromide (0.972 ml) was added dropwise at 0° C. and the resulting mixture was stirred at room temperature for 2.5 h. The reaction mixture was treated with ethanol (4 ml) and diluted with diethyl ether and the mixture was filtered. The filtrate was concentrated in vacuo to providing a crude residue which was purified by column chromatography (hexane/ethyl acetate 1:1) to give 2.33 g of 3-methyl-3-prop-2-ynyloxymethyl-1-oxa-4-aza-spiro[4.5]decane as an orange liquid. 1H NMR (CDCl3) δ ppm: 4.18 (2H, d); 3.82 (1H, d); 3.53 (1H, d); 3.43 (1H, d); 3.38 (1H, d); 2.42 (1H, t); 1.7-1.2 (10H, m); 1.25 (1H, s).

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