Diethyl Ether → 3-(4-Benzyloxyphenyl)-1-cyclopentylpropan-1-one
Reaktionsgleichung
N1C=CC=CC=1S[C:8](=[O:25])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1.[CH:26]1([Mg]Br)[CH2:30][CH2:29][CH2:28][CH2:27]1.CCOCC>C1COCC1>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][C:8]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:25])=[CH:16][CH:15]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
3-(4-Benzyloxyphenyl)thiopropionic acid S-pyridin-2-yl ester (3.00 g, 8.58 mmol) from Step 4 above was dissolved in dry THF (45 mL) and cooled to −78° C. A solution of cyclopentylmagnesium bromide in Et2O (2.0 M, 4.51 mL, 9.02 mmol) was added dropwise along the sides of the reaction vessel. After stirring 35 min, the cooling bath was removed. The reaction mixture was quenched with saturated aq. NH4Cl upon reaching ambient temperature and extracted with Et2O (500 mL). The organic phase was washed with brine (50 mL), dried over MgSO4 and evaporated. The residue was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (2.22 g, 84%) as a white semi-crystalline material. 1H NMR (CDCl3) δ 1.48-1.83 (m, 8H), 2.69-2.77 (m, 2H), 2.79-2.88 (m, 3H), 5.03 (s, 2H), 6.86-6.92 (m, 2H), 7.07-7.12 (m, 2H), 7.28-7.45 (m, 5H).
Aufarbeitung
- customthe cooling bath was removed
- customThe reaction mixture was quenched with saturated aq. NH4Cl
- customupon reaching ambient temperature
- extractionextracted with Et2O (500 mL)
- washThe organic phase was washed with brine (50 mL)
- dry with materialdried over MgSO4
- customevaporated
- customThe residue was purified by flash column chromatography (10% EtOAc in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-a0c13ef0c0de4b69b2beaa4e64e371b6
- Quelldatensatz
- uspto-grants-2009_01
- Patentnummer
- US07473790B2
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