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

HRID 498936Notes

Reaction equation

HRID 498936 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]=[O:15])[CH:5]=[C:4]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21])[C:3]1=2.[C:23]([Mg]Br)#[CH:24]>C1COCC1>[CH3:1][C:2]1([CH3:22])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([OH:15])[C:23]#[CH:24])[CH:5]=[C:4]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21])[C:3]1=2

Participants

4

Reactant 2

HCID 866125935,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 866125941-[5,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-olYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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%).

Workup

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

Sources & evidence

ORD record
ord-33f16609e517490ebf38d9da5002e465
Source dataset
uspto-grants-2010_08
Patent number
US07767650B2

Reaction notes

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