Hydrochloric Acid → (2R)-2-(1-hydroxy-1-(3-methoxyphenyl)methyl]cyclohexanone

HRID 377321

Reaktionsgleichung

C[O:2][C:3]1[CH:20]=[CH:19][CH:18]=[C:17](OC)[C:4]=1C([C@@]([C@H](C(O)=O)O)(O)C(O)=O)=O.C[Si](C)(C)OC1CCCCC=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=[O:40].Cl>C(#N)CC.O1CCCC1>[OH:40][CH:39]([C@H:4]1[CH2:17][CH2:18][CH2:19][CH2:20][C:3]1=[O:2])[C:38]1[CH:41]=[CH:42][CH:43]=[C:36]([O:35][CH3:34])[CH:37]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (R,R)-mono(2,6-dimethoxybenzoyl)tartaric acid (314 mg) in propionitrile (5 ml) was added 1M BH3 solution (1.0 ml) in tetrahydrofuran at 0° C. under N2. The reaction mixture was stirred for 1 hour at 0° C., and then the solution was cooled to -78° C. To this were added 1-(trimethylsilyl-oxy)cyclohexene (1.0 g) and 3-methoxybenzaldehyde (680 mg) successively. After stirring for 2 hours, the solution was poured into 1N-hydrochloric acid and the product was extracted with ether. The solvent was evaporated, and the residue was treated with 1N-hydrochloric acid-tetrahydrofuran solution (2 ml, 1:1). Usual chromatographic separation gave (2R)-2-(1-hydroxy-1-(3-methoxyphenyl)methyl]cyclohexanone (350 mg).

Aufarbeitung

temperaturethe solution was cooled to -78° C
stirringAfter stirring for 2 hours
extractionthe product was extracted with ether
customThe solvent was evaporated
additionthe residue was treated with 1N-hydrochloric acid-tetrahydrofuran solution (2 ml, 1:1)
customUsual chromatographic separation

Quellen und Nachweise

ORD-Eintrag: ord-2cf3118a80684934bb0069fd596a3ca9
Quelldatensatz: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06025375

Verknüpfte Notizen

Wird geladen…