Benzyl Alcohol → HCID 15042555, Verbindung

HRID 1761370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1761370
[C:1]([C:5]([CH3:11])([CH3:10])[CH2:6]C(O)=O)([O:3][CH3:4])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.C([N:31]([CH2:34]C)CC)C.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1>[CH2:36]([O:43][C:34]([NH:31][CH2:6][C:5]([CH3:11])([CH3:10])[C:1]([O:3][CH3:4])=[O:2])=[O:19])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 150395654-Methoxy-3,3-dimethyl-4-oxobutanoic acid

Produkt 1

HCID 15042555HCID 15042555, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

3-Carbomethoxy-3-methylbutanoic acid [Bull. Soc. Chim. Fr., 828 (1965), 7.85 g, 0.049 mol] was reacted with diphenylphosphorylazide and triethylamine as described in Example 36. After heating the toluene solution for 1.5 h, benzyl alcohol (8 g) was added directly to the reaction mixture and heating at reflux was continued for 20 h. Work-up and chromatography gave methyl 3-benzyloxycarbonylamino-2,2-dimethylpropionate. NMR (300 MHz, CDCl3): 1.2 (s,6H), 3.3 (d,2H), 3.68 (s,3H), 5.1 (s,2H), 5.22 (m,1H). A sample of the methyl ester (6.21 g, 0.023 mol) was saponified with 3.1 g (0.78 mol) of NaOH in 100 mL ethanol/10 mL H2O at room temperature for 48 h. Work-up as in Example 36 gave the desired product as a liquid. NMR (300 MHz, CDCl3): 1.23 (s,6H), 3.32 (d,2H), 5.10 (s,2H), 5.27 (m,1H).

Aufarbeitung

  1. temperatureheating
  2. temperatureat reflux

Quellen und Nachweise

ORD-Eintrag
ord-9d27bb2ef399462ea0c896addee302b2
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04826815

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