Borane → 2-(3-Iodophenyl)ethanol

HRID 15892

Reaktionsgleichung

Reaktionsgleichung von HRID 15892
B.[I:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](O)=[O:11])[CH:6]=[CH:7][CH:8]=1.[Cl-].[NH4+]>C1COCC1>[I:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 6331BoraneHCID 25517Ammonium ChlorideHCID 38702203-Iodophenylacetic acid

Produkt 1

HCID 151698502-(3-Iodophenyl)ethanolAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of borane (1M, THF, 2.5 eq., 38.2 mL) was added dropwise to a stirred solution of (3-iodophenyl)acetic acid (4.0 g) in THF (100 mL) cooled to 0 C. The resulting mixture was stirred at 0 C for 1 h then warmed to room temperature and stirred for a further 3 h. The mixture was poured into aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried (sodium sulfate) and concentrated. The crude was purified by column chromatography (SPE cartridge, SiO2), using cyclohexane-ethyl acetate (70:30) as eluent to afford the title compound (3.5 g, 92% yield).

Aufarbeitung

  1. temperaturecooled to 0 C
  2. stirringstirred for a further 3 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe crude was purified by column chromatography (SPE cartridge, SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-43c5c0c66d5a4557aba3851a4a0e8ac7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732600B2

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