2,4,5-Trifluorophenylacetic acid → 2-(2,4,5-Trifluorophenyl)ethan-1-ol

HRID 718358

Reaktionsgleichung

Reaktionsgleichung von HRID 718358
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11](O)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][CH2:11][OH:12]

Komponenten

4

Edukt 2

HCID 27779502,4,5-Trifluorophenylacetic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 177508392-(2,4,5-Trifluorophenyl)ethan-1-olAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-(2,4,5-trifluorophenyl)acetic acid (1 g, 5.26 mmol) in dry THF (20 mL) was carefully added over 2 min to solution of 2M LAH (10.52 mL, 10.52 mmol) at 0° C. The reaction mixture was allowed to warm to rt and was stirred for 6 h. The reaction was quenched with 0.5 mL of water (stir for 10 min), 0.5 mL of 15% NaOH/water (stir for 10 min), and then 1.0 mL of water. After stirring for 18 h, the mixture was filtered through celite. The filtrate was concentrated in vacuum. The residue was dried under high vacuum for 16 h to afford 2-(2,4,5-trifluorophenyl)ethanol (850 mg, 4.83 mmol, 92% yield) as a clear viscous oil, which was used as is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.11 (ddd, J=10.3, 8.7, 7.2 Hz, 1H), 6.93 (td, J=9.7, 6.6 Hz, 1H), 3.87 (t, J=6.5 Hz, 2H), 2.88 (t, J=6.5 Hz, 2H).

Aufarbeitung

  1. customThe reaction was quenched with 0.5 mL of water (stir for 10 min), 0.5 mL of 15% NaOH/water (stir for 10 min)
  2. stirringAfter stirring for 18 h
  3. filtrationthe mixture was filtered through celite
  4. concentrationThe filtrate was concentrated in vacuum
  5. customThe residue was dried under high vacuum for 16 h

Quellen und Nachweise

ORD-Eintrag
ord-f0a353c24d1b4510a32efe4af3ee6e52
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193720B2

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