Sodium hydride → 3-Ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone

HRID 1446981Notes

Reaction equation

HRID 1446981 reaction equation
[CH2:1]([O:3][C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH2:7][C:6](=[O:17])[CH:5]=1)[CH3:2].[H-].[Na+].[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25]Cl>O1CCCC1>[CH2:1]([O:3][C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:7][C:6](=[O:17])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 205521353-Ethoxy-5-(2-hydroxyphenyl)-2-cyclohexenone

Product 1

HCID 205521113-Ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenoneYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of 3-ethoxy-5-(2-hydroxyphenyl)-2-cyclohexenone (32.4 g) in tetrahydrofuran (400 ml) was added slowly to an ice-cooled suspension of sodium hydride (3.34 g) in tetrahydrofuran (75 ml). The mixture was stirred at room temperature for 30 min, cooled in an ice-bath and a solution of methoxyethoxymethyl chloride (20.8 g) in tetrahydrofuran (50 ml) was added dropwise with stirring. The mixture was stirred overnight at room temperature and then was concentrated by the removal of most of the tetrahydrofuran under reduced pressure. The concentrate was diluted with water and extracted with ether. The ethereal extracts were dried and the solvent removed under reduced pressure. The residual oil was purified by column chromatography on silica gel using chloroform for elution to afford the title compound (36.23 g) as a pale yellow oil.

Workup

  1. temperaturecooled
  2. temperaturecooled in an ice-bath
  3. stirringwith stirring
  4. stirringThe mixture was stirred overnight at room temperature
  5. concentrationwas concentrated by the removal of most of the tetrahydrofuran under reduced pressure
  6. additionThe concentrate was diluted with water
  7. extractionextracted with ether
  8. customThe ethereal extracts were dried
  9. customthe solvent removed under reduced pressure
  10. customThe residual oil was purified by column chromatography on silica gel
  11. washfor elution

Sources & evidence

ORD record
ord-36c00acceb7948dc887009367c8be83b
Source dataset
uspto-grants-1982_02
Patent number
US04315006

Reaction notes

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