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

HRID 1587876Notes

Reaction equation

HRID 1587876 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

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

  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-e48a477736d14b1080af998b887838cf
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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