Reaction #586118

Reaction equation

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

Yield 97.0%

Solvents

THF

Conditions

Workup

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

Procedure

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%).

Source