Ethyl Acetate → 2-(4-Bromophenyl)butan-1-ol

HRID 735694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735694
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH3:13])[C:9](O)=[O:10])=[CH:4][CH:3]=1.CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:12][CH3:13])[CH2:9][OH:10])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 8857Ethyl AcetateHCID 574722-(4-Bromophenyl)butanoic acid

Produkt 1

HCID 578429142-(4-Bromophenyl)butan-1-olAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 75B (96 mg, 0.4 mmol) in 3 mL THF was added BH3 (2M in THF, 0.5 mL, 1 mmol). The solution was stirred at rt for 16 h. EtOAc (20 mL) was added, and the organic phase washed with 1M H3PO4, sat. NaHCO3 and brine, dried (Na2SO4), and concentrated. Purification via flash chromatography (0-30% EtOAc in hexanes) gives 75C (86 mg, 96%). MS (ESI) m/z 211.2(M−H2O)+.

Aufarbeitung

  1. washthe organic phase washed with 1M H3PO4, sat. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification via flash chromatography (0-30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-331f3055c50e409397c439801d9504f2
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592331B2

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