반응 #586118

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5,5,8,8-tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

ethynylmagnesium bromide

→

1-[5,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-ol

수율 97.0%

용매

THF

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후처리

1. 1
   추출After treatment with 1N hydrochloric acid solution and extraction with ethyl acetate
2. 2
   기타followed by evaporation
3. 3
   기타the residue is purified by chromatography on a column of silica (eluent: 8/2 heptane/EtOAC)
4. 4
   기타A yellow oil is obtained (m=42 g; yield=97%)

실험 절차

40 g (131 mmol) of 5,5,8,8-tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of THF. 290 mL (145 mmol) of 0.5N ethynylmagnesium bromide solution are added and the reaction medium is then stirred for 1 hour. After treatment with 1N hydrochloric acid solution and extraction with ethyl acetate, followed by evaporation, the residue is purified by chromatography on a column of silica (eluent: 8/2 heptane/EtOAC). A yellow oil is obtained (m=42 g; yield=97%).

출처