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

HRID 1616691Notes

Reaction equation

HRID 1616691 reaction equation
[CH3:1][C:2]1(C)[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].[CH2:27]1COCC1>>[CH3:1][CH:2]1[CH:11]([CH3:27])[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 3

HCID 8028TetrahydrofuranHCID 866125935,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 866698381-[5,6,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-olYield 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%).

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-26fedfb27ab74a9e9c216542255187d1
Source dataset
uspto-grants-2014_07
Patent number
US08765805B2

Reaction notes

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