Borane → 3-(3-Nitrophenyl)propan-1-ol

HRID 1614959Notes

Reaction equation

HRID 1614959 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12](O)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].B>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 27602243-(3-Nitrophenyl)propionic acid

Product 1

HCID 113328423-(3-Nitrophenyl)propan-1-olYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(3-Nitrophenyl)propanoic acid (3.0 g, 15 mmol) was dissolved in dry tetrahydrofuran (7.6 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (20 mL, 20 mmol, 1.0 M) was added dropwise over a period of 30 minutes. The reaction mixture was stirred for an additional 2 hours at rt, then quenched slowly with ice water, and followed by an addition of ether (40 mL). The ether layer was washed with water and saturated aqueous solution of NaHCO3 successively, dried, and concentrated to give the desired product as a yellow gel (2.7 g, 97%).

Workup

  1. temperaturecooled in an ice bath
  2. customquenched slowly with ice water
  3. additionfollowed by an addition of ether (40 mL)
  4. washThe ether layer was washed with water and saturated aqueous solution of NaHCO3 successively
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c957fe516c334ecbad392a474746ab61
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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