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

HRID 484331Notes

Reaction equation

HRID 484331 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-dihydrobenzofuran-5-yl) 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 (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2×50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, (3.3 g).

Workup

  1. filtrationThe mixture was filtered
  2. washthe inorganic salts washed with ethyl acetate (2×50 ml)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08ba30a820e94f7898d62aca50241d86
Source dataset
uspto-grants-1993_07
Patent number
US05231104

Reaction notes

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