Sodium Hydroxide → [5-(2-Methyl-1,3-dioxolan-2-yl)thien-2-yl]methanol

HRID 1271112Notes

Reaction equation

HRID 1271112 reaction equation
C(C1S[C:7]([C:9]([OH:11])=O)=CC=1)(=O)C.[OH2:12].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](O)(=O)=O)=[CH:15][CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-:30].[Na+]>C1COCC1.C1(C)C=CC=CC=1.C(O)CO>[CH3:14][C:15]1([C:16]2[S:19][C:13]([CH2:23][OH:30])=[CH:18][CH:17]=2)[O:11][CH2:9][CH2:7][O:12]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 37427275-Acetylthiophene-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 23021247[5-(2-Methyl-1,3-dioxolan-2-yl)thien-2-yl]methanol

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 5-acetylthiophene-2-carboxylic acid (41.44 g), p-toluenesulfonic acid monohydrate (926 mg), ethylene glycol (226 g) and toluene (500 ml) was refluxed under heating for 13 hours and subjected to azeotropic dehydration. The reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a brawn solution. This product was dissolved in THF (500 ml) and the solution was gradually dropped to a mixture of lithium aluminum hydride (19.22 g) and THF (750 ml) under ice cooling. Two hours later, thereto was added a 10% aqueous sodium hydroxide solution (1000 ml). After the removal of insoluble materials, the filtrate was extracted with ethyl acetate. The organic layer was washed with water (twice) and was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give [5-(2-methyl-1,3-dioxolan-2-yl)thien-2-yl]methanol. This product was used in the next step without purification.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 13 hours
  3. washThe reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customto give a brawn solution
  7. customAfter the removal of insoluble materials
  8. extractionthe filtrate was extracted with ethyl acetate
  9. washThe organic layer was washed with water (twice) and
  10. dry with materialwas dried over anhydrous sodium sulfate
  11. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f5487a4fa5cf46f59319d8bfd5cd05ef
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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