Tetrahydrofuran → Methyl 2-methyl-4-hydroxybutyrate

HRID 2294666

Reaktionsgleichung

Reaktionsgleichung von HRID 2294666
[CH3:1][O:2][C:3](=[O:9])[CH:4]([CH3:8])[CH2:5][C:6]#N.C1C[O:13]CC1.C1CCCCCCCCCCC1.CC1CCOC1=O>O>[CH3:8][CH:4]([CH2:5][CH2:6][OH:13])[C:3]([O:2][CH3:1])=[O:9]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 9268CyclododecaneHCID 98323alpha-MethylbutyrolactoneHCID 3016095Methyl 3-cyano-2-methylpropionate

Produkt 1

HCID 12953943Methyl 2-methyl-4-hydroxybutyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 0.05 mmol RuHCl(H2)(PCy3)2, 0.54 mmol methyl-3-cyano-isobutyrate (prepared by addition of HCN to methyl methacrylate), 17.7 g THF, 15.3 g water, and 0.0596 g cyclododecane (internal standard for gc analysis) was stirred in an autoclave and heated to 100° C. under 7000 kPa H2. After 3.2 hours, the nitrile was completely and cleanly converted to methyl-butyrolactone, which formed by transesterification/cyclization of the intermediate hydroxyester, methyl 2-methyl-4-hydroxybutyrate.

Quellen und Nachweise

ORD-Eintrag
ord-03ca15f901d241dba41af4b0d6fa2a52
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05689003

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