Aluminium lithium hydride → 5-[3-(Methyloxy)propyl]-2-(methylthio)benzyl alcohol

HRID 337623Notes

Reaction equation

HRID 337623 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([S:16][CH3:17])=[C:10]([CH:15]=1)[C:11](OC)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([S:16][CH3:17])=[C:10]([CH:15]=1)[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66896180Methyl 5-[3-(methyloxy)propyl]-2-(methylthio)benzoate

Product 1

HCID 668961945-[3-(Methyloxy)propyl]-2-(methylthio)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-[3-(methyloxy)propyl]-2-(methylthio)benzoate (1 eq.) from the previous step was taken up in THF (0.1 M) and then added lithium aluminum hydride (1 eq.). The reaction mixture thus obtained was stirred at RT for 16 h. The reaction was then quenched with 1 N aq. HCl and extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a white solid.

Workup

  1. customThe reaction mixture thus obtained
  2. customThe reaction was then quenched with 1 N aq. HCl
  3. extractionextracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-3cc63f28b69e4535b64a4ed85577cdee
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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