1-Tetralone → (R)-(-)-1,2,3,4-Tetrahydro-1-naphthol

Reaktionsgleichung

[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1>CC(O)C>[CH2:1]1[CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C@H:9]([OH:10])[CH2:11]1

Komponenten

Reaktionsbedingungen

Temperatur: 35 °C

Versuchsvorschrift

Sodium 2-propoxide (0.38 ml of 0.1M solution in 2-propanol) was charged to the catalyst solution followed by the α-tetralone (0.5 ml, 3.76 mmol). The mixture was stirred under vacuum (80 mmHg) at 35° C. for 2 h, after the first hour the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 98.4%, ee 95.7%. The turnover number, integrated over 1 h, was 185 h−1

Aufarbeitung

additioncharged
customremoved by distillation

Quellen und Nachweise

ORD-Eintrag: ord-8acfcadd05e7439cb808001111c7a19c
Quelldatensatz: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06545188B2

Notizen zur Reaktion

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Komponenten

Edukt 1

HCID 107241-Tetralone

Produkt 1

HCID 7058028(R)-(-)-1,2,3,4-Tetrahydro-1-naphtholAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel