Water → 2-(2,3-Dihydro-1-benzofuran-5-yl)ethan-1-ol

HRID 375578Notes

Reaction equation

HRID 375578 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11](O)=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:12][CH2:11][CH2:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27374552,3-Dihydro-5-benzofuranacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 212240782-(2,3-Dihydro-1-benzofuran-5-yl)ethan-1-olYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2,3-dihydro-5-benzofuranyl)acetic acid (4.9 g--see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide solution (1.5 ml) and water (4.5 ml). The mixture was filtered and the inorganic salts were washed with ethyl acetate. The filtrate and washings were combined and evaporated to give the title compound as an oil, (3.3 g), which was characterised by its 1H-NMR spectrum.

Workup

  1. filtrationThe mixture was filtered
  2. washthe inorganic salts were washed with ethyl acetate
  3. customevaporated

Sources & evidence

ORD record
ord-5906822431a24b8ea04730d6939a6e27
Source dataset
uspto-grants-1996_01
Patent number
US05486527

Reaction notes

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