Tetrahydrofuran → 9-Ethyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418952
COC1[CH:4]=[C:5]2[C:14](=[CH:15]C=1)[CH:13](COS(C1C=CC(C)=CC=1)(=O)=O)[CH:12]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[CH3:37][Mg]Br.[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH2:14]([CH:13]1[CH:12]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[C:5]2[C:41]1=[CH:42][CH:43]=[C:44]([O:40][CH3:37])[CH:4]=2)[CH3:15]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl esterHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 666519649-Ethyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneAusbeute 81 %

Versuchsvorschrift

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.151 g, 0.30 mmol), methyl magnesium bromide (0.46 mL, 1.40 mmol), Li2CuCl4 (150 uL), and tetrahydrofuran (3 mL), and stir under nitrogen atmosphere. After 18 hours, concentrate reaction under vacuum and flash chromatograph using 0% to 10% ethyl acetate/hexanes to yield the titled compound (0.085 g, 81%) as a white foam. TLC Rf=0.60 in 8:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.32 (s, 1H), 7.24 (d, 2H, J=8.4 Hz), 6.94 (m, 3H), 6.81 (dd, 1H, J=8.4, 2.6 Hz), 3.86 (m, 6H), 3.42 (m, 1H), 3.23 (s, 1H), 3.08 (dd, 1H, J=12.1, 3.3 Hz), 2.49 (d, 1H, J=13.7 Hz), 1.93 (m, 2H), 1.67 (m, 1H), 1.57 (m, 2H), 1.44 (d, 2H, J=8.8 Hz), 1.19 (m, 3H), 0.62 (t, 3H, J=7.3 Hz).

Aufarbeitung

  1. concentrationconcentrate
  2. customreaction under vacuum and flash chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-aca86e55c0e2414c9b5f8465dc0d507e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093302B2

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