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

HRID 2253906Notes

Reaction equation

HRID 2253906 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 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, 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-6e07ffbc403043a5b13280c8aa87aa61
Source dataset
uspto-grants-1993_08
Patent number
US05233053

Reaction notes

Loading…