Cesium carbonate → 3-(4-{1-Ethyl-1-[4-(3-hydroxy-3-methylbutyl)-3-methylphenyl]-propyl}-2-methylphenoxy)-propane-1,2(S)-diol

HRID 250174

Reaktionsgleichung

Reaktionsgleichung von HRID 250174
[CH2:1]([C:3]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])=[C:8]([CH3:18])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[F-].[Cs+].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:35]1[O:37][C@H:36]1[CH2:38][OH:39]>C(Cl)Cl.CN(C=O)C>[CH2:1]([C:3]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:35][C@@H:36]([OH:37])[CH2:38][OH:39])=[C:21]([CH3:26])[CH:20]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:17])([CH3:15])[CH3:16])=[C:8]([CH3:18])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 6973630(-)-GlycidolHCID 574330374-{1-Ethyl-1-[4-(3-hydroxy-3-methylbutyl)-3-methyl-phenyl]propyl}-2-methylphenol

Produkt 1

HCID 113737463-(4-{1-Ethyl-1-[4-(3-hydroxy-3-methylbutyl)-3-methylphenyl]-propyl}-2-methylphenoxy)-propane-1,2(S)-diolAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-{1-ethyl-1-[4-(3-hydroxy-3-methylbutyl)-3-methyl-phenyl]propyl}-2-methylphenol (0.14 g, 0.40 mmol) in anhyd DMF (2 mL) was added CsF (67 mg, 0.44 mmol), Cs2CO3 (26 mg, 80 □ mol) and (S)-glycidol (29 μL, 0.44 mmol). The reaction mixture was heated at 80° C. for 4 h. After cooling, the mixture was diluted with DCM (40 mL), washed with H2O (2×40 mL), 1 N HCl (20 mL) and brine, then dried (Na2SO4) and concentrated under reduced pressure. The crude material was chromatographed (silica, EtOAc/DCM, 0:100 to 75:25) to provide the title compound (80 mg, 47%) as a white powdered solid: 1H-NMR (CD2Cl2) δ 7.01 (1H, d, J=8.1), 6.96 (1H, dd, J=2.3, 8.3), 6.88-6.94 (3H, m), 6.73 (1H, d, J=8.3), 3.97-4.11 (3H, m), 3.77-3.84 (1H, m), 3.69-3.76 (1H, m), 2.62 (2H, m), 2.53 (1H, d, J=5.1), 2.24 (3H, s), 2.16 (3H, s), 2.05 (4H, q, J=7.3), 1.99 (1H, t, J=6.1), 1.67 (2H, m), 1.27 (6H, s), 0.58 (6H, t, J=7.3); 13C-NMR (CD2Cl2) δ 155.0, 147.2, 142.0, 138.4, 135.7, 131.2, 130.4, 128.5, 126.9, 126.3, 126.2, 110.9, 71.4, 71.3, 70.1, 64.6, 49.3, 45.2, 29.8, 29.6, 28.3, 20.0, 17.0, 8.9.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with H2O (2×40 mL), 1 N HCl (20 mL) and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was chromatographed (silica, EtOAc/DCM, 0:100 to 75:25)

Quellen und Nachweise

ORD-Eintrag
ord-59e1bc07dd7d4d30bfa3e5531c27f90e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863298B2

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