Borane → 3-(Furan-2-yl)propan-1-ol

HRID 1888632

Reaktionsgleichung

Reaktionsgleichung von HRID 1888632
[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]

Komponenten

4

Edukt 2

HCID 6331BoraneHCID 702862-Furanpropionic acid

Produkt 1

HCID 2271783-(Furan-2-yl)propan-1-olAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-926d7726ff974b7284aa7dd74f59f530
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501794B2

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