Hydrochloric Acid → 3-(2,3-Dihydro-1-benzofuran-5-yl)propan-1-ol

HRID 1093468Notes

Reaction equation

HRID 1093468 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12](O)=[O:13])=[CH:9][C:4]=2[CH2:3][CH2:2]1.O1CCCC1.B.O.Cl>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 28154053-(2,3-Dihydro-1-benzofuran-5-yl)propanoic acid

Product 1

HCID 534250023-(2,3-Dihydro-1-benzofuran-5-yl)propan-1-olYield 103%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(2,3-Dihydrobenzofuran-5-yl)propionic acid (2.00 g) was dissolved in tetrahydrofuran (20 ml), and a tetrahydrofuran-borane.tetrahydrofuran solution (1 mol/l, 11.5 ml) was added dropwise to the mixture under ice-cooling. The mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 16 hr. Water was added to the reaction mixture, and 1M aqueous hydrochloric acid solution was added. The mixture was extracted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the object product (1.91 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-92bd6c83ced041d09f489f479e3424ed
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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