Borane → 3-(Furan-2-yl)propan-1-ol

HRID 253621

Reaction equation

HRID 253621 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8](O)=[O:9].B>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9]

Participants

4

Reactant 2

HCID 6331BoraneHCID 702862-Furanpropionic acid

Product 1

HCID 2271783-(Furan-2-yl)propan-1-olYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-(furan-2-yl)propanoic acid (1.4 g, 10 mmol) in THF (50 mL) was added dropwise borane (1M) (20 mL, 20 mmol). The mixture was stirred at rt for 12 hrs, quenched with MeOH, and the mixture was concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.0 g (79%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.87-1.94 (m, 2H) 2.74 (t, J=7.32 Hz, 2H) 3.69 (t, J=6.10 Hz, 2H) 6.28 (dd, J=3.05, 1.83 Hz, 1H) 7.30 (d, J=0.92 Hz, 1H).

Workup

  1. customquenched with MeOH
  2. concentrationthe mixture was concentrated
  3. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-d0c92ca741574291a86f4d3a42c94f59
Source dataset
uspto-grants-2011_01
Patent number
US07872033B2

Linked notes

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