Reaktionsgleichung
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:12]1[O:16][C:15]([C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:18])=[CH:14][CH:13]=1>CN1C(=O)CCC1>[CH:1]1([CH2:7][O:8][C:12]2[O:16][C:15]([C:17]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:18])=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Cyclohexylmethanol (1.60 g, 14.0 mmol) was slowly added to a cooled (0° C.) suspension of sodium hydride (0.30 g, 12.5 mmol) in anhydrous NMP (5 mL) under Ar. A solution of cyclohexylmethyl 5-bromofuran-2-carboxylate (1.79 g, 6.23 mmol) in anhydrous NMP (6 mL) was added to the reaction mixture and stirred overnight at room temperature. The reaction mixture was partitioned between aqueous NH4Cl (25%) and hexanes. Aqueous layer was extracted with hexanes and combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography (2%-10% EtOAc—hexanes gradient) gave cyclohexylmethyl 5-(cyclohexylmethoxy)furan-2-carboxylate as a colorless oil. Yield (1.05 g, 53%); 1H NMR (400 MHz, CDCl3) δ 7.10 (d, J=3.4 Hz, 1H), 5.27 (d, J=3.9 Hz, 1H), 4.05 (d, J=6.4 Hz, 2H), 3.91 (d, J=5.9 Hz, 2H), 1.62-1.85 (m, 12H), 1.10-1.33 (m, 6H), 0.94-1.10 (m, 4H).
Aufarbeitung
- temperaturea cooled
- customThe reaction mixture was partitioned between aqueous NH4Cl (25%) and hexanes
- extractionAqueous layer was extracted with hexanes
- washwere washed with brine
- concentrationconcentrated under reduced pressure
- customPurification by flash chromatography (2%-10% EtOAc—hexanes gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-153e5b217a6840708a3c71eb2e2a633a
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09447078B2
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