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

HRID 561928ノート

反応式

HRID 561928 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5863dadcee1842a49c3376326e6ab7e8
出典データセット
uspto-grants-2011_11
特許番号
US08063225B2

反応ノート

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