Chloromethyl Methyl Ether → 2-(6-Bromo-3-methoxy-2-methoxymethoxy-phenyl)-5,5-dimethyl-[1,3]dioxane

HRID 929111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929111
[Br:1][C:2]1[C:3]([CH:11]2[O:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][O:12]2)=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.Cl[CH2:29][O:30][CH3:31]>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH:11]2[O:12][CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][O:16]2)=[C:4]([O:10][CH2:29][O:30][CH3:31])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 597618363-Bromo-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-methoxy-phenol

Produkt 1

HCID 597618382-(6-Bromo-3-methoxy-2-methoxymethoxy-phenyl)-5,5-dimethyl-[1,3]dioxane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the solution of 3-bromo-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-methoxy-phenol in DCM (20 mL) was added DIEA (697 μL, 4 mmol), followed by addition of chloromethoxymethane (228 μL, 3 mmol). After it was stirred at the room temperature for 72 h, the reaction mixture was evaporated and the residue was partitioned between NaHCO3 (50 mL) solution and EtOAc (40 mL). The aqueous layer was extracted with EtOAc (3×10 mL) and the combined extracts were washed with brine and dried through Na2SO4. Evaporation of solvent afforded the title compound. 1H NMR (CDCl3) δ 0.80 (s, 3H), 1.45 (s, 3H), 3.57 (s, 3H), 3.65 (d, J=12 Hz, 2H), 3.79 (s, 3H), 3.80 (d, J=12 Hz, 2H), 5.11 (s, 2H), 6.00 (s, 1H), 6.76 (d, J=8 Hz, 1H), 7.32 (d, J=8 Hz, 1H).

Aufarbeitung

  1. customthe reaction mixture was evaporated
  2. customthe residue was partitioned between NaHCO3 (50 mL) solution and EtOAc (40 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  4. washthe combined extracts were washed with brine
  5. dry with materialdried through Na2SO4
  6. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-d164b3c94a3e4fcba144442f301fb8cf
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290503B2

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