Water → 2-(2,3-Dihydro-1-benzofuran-5-yl)ethan-1-ol
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]=1Participants
6
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 over 10 minutes, dropwise, to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0°. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was then added dropwise with caution 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, yield 3.3 g.
Workup
- filtrationThe mixture was filtered
- washthe inorganic salts washed with ethyl acetate (2×50 ml)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-913cf6713d034601b997f0144d1fe970
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05192765
Reaction notes
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