(2R)-1-(benzyloxy)pent-4-en-2-ol → (2R)-1-(benzyloxy)hex-4-en-2-ol

HRID 590602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590602
[CH2:1]([O:8][CH2:9][C@H:10]([OH:14])[CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]([Mg]Br)=CC>>[CH2:1]([O:8][CH2:9][C@H:10]([OH:14])[CH2:11][CH:12]=[CH:13][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 10375318(2R)-1-(benzyloxy)pent-4-en-2-olHCID 178456053HCID 178456053, Verbindung

Produkt 1

HCID 71352308(2R)-1-(benzyloxy)hex-4-en-2-ol

Versuchsvorschrift

The product was obtained according to the method used for synthesis of (2R)-1-(benzyloxy)pent-4-en-2-ol (C1) in Preparation P1, except that 1-propenylmagnesium bromide was used in place of vinylmagnesium bromide. The product was obtained as a brown oil, which was used without further purification; by 1H NMR, this material consisted of a 1:1 mixture of geometric isomers. Yield: 140 g, 0.679 mol, 100%. 1H NMR (400 MHz, CDCl3) δ 7.28-7.42 (m, 5H), 5.39-5.67 (m, 2H), 4.57 (s, 2H), 3.80-3.92 (m, 1H), 3.48-3.57 (m, 1H), 3.35-3.43 (m, 1H), 2.36-2.50 (br m, 1H), 2.24-2.33 (m, 1H), 2.17-2.24 (m, 1H), [1.68 (br d, J=6 Hz) and 1.64 (br d, J=7 Hz), total 3H].

Aufarbeitung

  1. customThe product was obtained
  2. customThe product was obtained as a brown oil, which
  3. customwas used without further purification
  4. additionby 1H NMR, this material consisted of a 1:1 mixture of geometric isomers

Quellen und Nachweise

ORD-Eintrag
ord-5ad5db124f0147138bf401b3f2c803f2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233981B1

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