Borane → 3-(Furan-2-yl)propan-1-ol

HRID 76260

Reaction equation

HRID 76260 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-bf8a3094c84c47e28c70980942e125b2
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Linked notes

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