Pyrogallol → 4-(3,5-Dimethoxy-benzyloxy)-2-ethoxy-benzo[1,3]dioxole

HRID 1976214ノート

反応式

HRID 1976214 の反応式
[CH2:1]([O:3][CH:4]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:6]=2[O:5]1)[CH3:2].BrC[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[O:24][CH3:25].[C:26](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.C1(C=CC=C(O)C=1O)O>CC(C)=O>[CH3:23][O:22][C:19]1[CH:20]=[C:21]([CH:16]=[C:17]([O:24][CH3:25])[CH:18]=1)[CH2:26][O:13][C:12]1[C:6]2[O:5][CH:4]([O:3][CH2:1][CH3:2])[O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

参加物

7

反応物 5

HCID 1057PyrogallolHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 134470632-Ethoxy-benzo[1,3]dioxol-4-olHCID 151519071-(Bromomethyl)-2,4-dimethoxybenzene

生成物 1

HCID 220006654-(3,5-Dimethoxy-benzyloxy)-2-ethoxy-benzo[1,3]dioxole

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

2-Ethoxy-benzo[1,3]dioxol-4-ol (1.11 g, 6.08 mmol), 4-bromomethyl-1,3-dimethoxybenzene (1.17 g, 5.08 mmol), potassium carbonate (0.77 g, 5.59 mmol) and 18-crown-6-ether (0.13 g, 0.51 mmol) were stirred together at room temperature in acetone (40 cm3, 99%) under nitrogen for 18 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (30 cm3) and water (30 cm3). The aqueous layer was extracted with dichloromethane (3×30 cm3), and the combined extracts were washed with water (2×50 cm3), dried (MgSO4), and evaporated under reduced pressure. The residue was chromatographed (SiO2, dichloromethane) to give the di protected pyrogallol, (1.56 g, 92%) as a clear oil.

後処理

  1. customThe solution was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted with dichloromethane (3×30 cm3)
  3. washthe combined extracts were washed with water (2×50 cm3)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed (SiO2, dichloromethane)
  7. customto give the di

出典と根拠

ORDレコード
ord-644d4b1f7098443785983ae2a6c8536d
出典データセット
uspto-grants-2001_05
特許番号
US06225352B1

反応ノート

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