HCID 57435888, Verbindung → 931430-20-5

HRID 30580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30580
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:5]=[CH:6][CH:7]=1.[H][H]>[Pt]=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 57435888HCID 57435888, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 57435887931430-20-5Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 82844Platinum oxide (PtO)Katalysator

Versuchsvorschrift

A mixture of an ethanolic solution of 5-(3-Bromo-phenyl)-pent-4-yn-1-ol (Example 3, step a) (1 g, 4.2 mmol)and platinum oxide (24 mg, 10% mol) was placed on a parr shaker for 4 hrs under 40 psi of hydrogen. The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo. The resultant residu was purified by flash chromatography on silica gel, 1st 10:1 hexane/ ethyl acetate, 2nd 2:1 hexane/ethyl acetate as eluent, to give 5-(3-bromophenyl)pentan-1-ol as a clear oil, 0.75 g (74% yield); 1H NMR (DMSO-d6) δ 1.2 (m, 2H); 1.3 (m, 2H); 1.5 (m, 2 H); 3.3 (q, 2H); 4.3 (t, 1 H); 7.2 (m, 2 H); 7.4 (m, 2 H) MS [(+)ESI] m/z=243 [M−H]+.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe resultant residu was purified by flash chromatography on silica gel, 1st 10:1 hexane/ ethyl acetate, 2nd 2:1 hexane/ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-bfb46ea0b2f246ce94355b728aa1628e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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