Allyl bromide → Methyl 2-ethyl-2-(1-methylethyl)-4-pentenoate

HRID 1955694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955694
[CH2:1]([CH:3]([CH:8]([CH3:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:2].[CH2:11](Br)[CH:12]=[CH2:13].C([N-]C(C)C)(C)C.[Li+].CN(P(N(C)C)(N(C)C)=O)C>C1COCC1>[CH2:1]([C:3]([CH:8]([CH3:10])[CH3:9])([CH2:13][CH:12]=[CH2:11])[C:4]([O:6][CH3:7])=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 7841Allyl bromideHCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 12696465Methyl 2-ethyl-3-methylbutyrate

Produkt 1

HCID 10607559Methyl 2-ethyl-2-(1-methylethyl)-4-pentenoateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The reaction of methyl 2-ethyl-3-methylbutyrate (23.76 g, 165 mmol), prepared as in Lion C, Dubois J E (1981) supra., with allyl bromide (31.34 g, 259 mmol) in the presence of lithium diisopropylamide (prepared by treating diisopropylamine (25.05 g, 248 mmol) with butyllithium in hexanes (2.5M, 94.4 mL, 236 mmol)) in THF (330 mL) and HMPA (24.7 mL, 142 mmol), as described above in the preparation of Example 7, followed by the vacuum distillation of crude product afforded the pure olefinic ester (24.85 g, 82%) as a colorless liquid: bp 92°-94° C. (20 mmHg).

Aufarbeitung

  1. distillationfollowed by the vacuum distillation of crude product

Quellen und Nachweise

ORD-Eintrag
ord-d9e5479a6ddb42ca8c9810fb47ac4276
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05776959

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