Borane → 3-(Furan-2-yl)propan-1-ol

HRID 1888632Notes

Reaction equation

HRID 1888632 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, 2 H) 2.74 (t, J=7.32 Hz, 2 H) 3.69 (t, J=6.10 Hz, 2 H) 6.28 (dd, J=3.05, 1.83 Hz, 1 H) 7.30 (d, J=0.92 Hz, 1 H).

Workup

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

Sources & evidence

ORD record
ord-926d7726ff974b7284aa7dd74f59f530
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

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