Acetic Acid → t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate

HRID 1107175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107175
C([O:9][CH2:10]/[C:11](/[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[OH:9][CH2:10]/[C:11](=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)/[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 69907940(E)-2-t-Butoxycarbonyl-7-phenylhept-2-enyl benzoate

Produkt 1

HCID 86755388t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(E)-2-t-Butoxycarbonyl-7-phenylhept-2-enyl benzoate (5.9 g, 15 mmol) is dissolved in MeOH (75 mL) and cooled to 0° C. K2CO3 (2 g, 15 mmol) is added with stirring and the reaction is allowed to warm to 23° C. After 2 hours the reaction is neutralized with HOAc and the reaction is concentrated to approximately half of its volume. After diluting with ether (500 mL), the solution is washed with water (50 mL) and brine (50 mL). The resulting solution is dried (MgSO4) and concentrated in vacuo. The crude reaction mixture is purified by column chromatography (silica, 25% ether in petroleum ether) to give t-butyl (E)-2-hydroxymethyl-7-phenylhept-2-enoate (2.2 g, 51%): 1H NMR (300 MHz, CDCl3) δ 7.30-7.25 (m, 2H), 7.20-7.15 (m, 3H), 6.75 (t, J=7.7 Hz, 1H), 4.28 (d, J=6.8 Hz, 2H), 2.65-2.60 (m, 3H), 2.26 (q, J=7.5 Hz, 2H), 1.71-1.61 (m, 2H), 1.53-1.43 (m, 11H).

Aufarbeitung

  1. temperatureto warm to 23° C
  2. concentrationthe reaction is concentrated to approximately half of its volume
  3. additionAfter diluting with ether (500 mL)
  4. washthe solution is washed with water (50 mL) and brine (50 mL)
  5. dry with materialThe resulting solution is dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customis purified by column chromatography (silica, 25% ether in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-f7a879bc6a8847aa9e9f30d2f6deb0d2
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057369

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