Water → HCID 67484566, Verbindung

HRID 397197

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:18])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)=[N+]=[N-].[CH:19]1([OH:25])[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1.O>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)[O:25][CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

A solution of (3-chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester (Example 6; 489 mg, 1.69 mmol) in dichloromethane (10 ML) at 25° C. was treated with 2-cyclohexen-1-ol (0.42 mL, 4.23 mmol) followed by rhodium (II) acetate dimer (15 mg, 0.034 mmol) and the resulting solution was stirred at 25° C. for 1 h. The reaction mixture was diluted with dichloromethane (10 mL), then was poured into water (15 mL) and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography (Biotage Flash 40S column, 75/25 hexanes/ethyl acetate) provided rac-(3-chloro-4-methanesulfonyl-phenyl)-(cyclohex-2-enyloxy)-acetic acid methyl ester (350 mg, 58% yield) as a colorless oil: EI-HRMS m/e calcd for C16H19ClSO5 (M+) 358.0642, found 358.0640.

Aufarbeitung

extractionextracted with dichloromethane (3×10 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe product was purified by chromatography (Biotage Flash 40S column, 75/25 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-af9c7fc4d707438fb8b14cbd44dacb9f
Quelldatensatz: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06608218B2

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