반응 #214746

반응 방정식

chloride

n-Butyllithium

6,6-Ethylenedioxy-2-methyl-heptanol

tetrahydrofuran

Methoxyethoxymethyl chloride

→

6,6-ethylenedioxy-1-methoxyethoxymethoxy-2-methylheptane

반응 조건

후처리

1. 1
   온도the solution is warmed to 0° C
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITis continued at 0° C. for 2 hours
4. 4
   기타The tetrahydrofuran is evaporated in vacuo
5. 5
   기타the residue is partitioned between ether and brine
6. 6
   추출The ether extract
7. 7
   건조is dried (Na2SO4)
8. 8
   기타the solvent is evaporated in vacuo

실험 절차

6,6-Ethylenedioxy-2-methyl-heptanol (2.0 g) is dissolved in anhydrous tetrahydrofuran (35 ml) and cooled to -78° C. under nitrogen. n-Butyllithium (0.68 g) is added and the solution is warmed to 0° C. Methoxyethoxymethyl chloride (1.59 g) is added and the reaction stirred at 0° C. for 1.5 hours. An additional 1.59 g of the chloride is added and stirring is continued at 0° C. for 2 hours. The tetrahydrofuran is evaporated in vacuo and the residue is partitioned between ether and brine. The ether extract is dried (Na2SO4) and the solvent is evaporated in vacuo to give 6,6-ethylenedioxy-1-methoxyethoxymethoxy-2-methylheptane. The compound is dissolved in acetone (40 ml) and 10% hydrochloric acid (2.0 ml) is added and the resulting solution is stirred for two hours. A saturated sodium bicarbonate solution (50 ml) is added, and the resulting precipitate filtered and the filtrate evaporated in vacuo. The residue is partitioned between ether and brine and the ether extract is dried (Na2SO4) and evporated in vacuo. The residue is chromatographed on silica (solvent: ethyl acetate/hexane) to give 1-methoxyethoxymethoxy-2-methyl-6-oxo-heptane as a colorless liquid, nmr (CDCl3,δ) 0.9 (d, CH3CH), 2.12 (s, CH3C=O), 2.4 (t, --CH2C=O, 3.3-3.8 (m, --OCH3, ##STR44## --OCH2CH2O), 4.66 (s, 2H, --OCH2O--).

출처