Water → 2-Methoxymethyloxy-3,4,5,6-tetramethoxybenzaldehyde

HRID 1770241ノート

反応式

HRID 1770241 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[C:6]=1[O:17][CH3:18].C([Li])CCC.CN([CH:27]=[O:28])C.O>CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([O:17][CH3:18])=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[C:10]=1[CH:27]=[O:28]

参加物

6

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 134955321-Methoxymethyloxy-2,3,4,5-tetramethoxybenzeneHCID 178418339Butyllithium

生成物 1

HCID 134955502-Methoxymethyloxy-3,4,5,6-tetramethoxybenzaldehyde

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-20 °C

実験手順

6.2 g of 1-methoxymethyloxy-2,3,4,5-tetramethoxybenzene prepared in Referential Example 13 was dissolved in 50 ml of anhydrous ether, and 18 ml of n-butyllithium (1.6M n-hexane solution) was dropwise added thereto at -20° C. while stirring. After the mixture was stirred at 0° C. for 30 min, the temperature was returned to -20° C. and 3.5 ml of DMF was dropwise added thereto. After 100 ml of water was added thereto, the mixture was extracted with ethyl acetate, and the organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3) to prepare 5.6 g of the product compound as a light yellow oleaginous substance.

後処理

  1. stirringAfter the mixture was stirred at 0° C. for 30 min
  2. customwas returned to -20° C.
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3)
  8. customto prepare 5.6 g of the product compound as a light yellow oleaginous substance

出典と根拠

ORDレコード
ord-73a55a75cb0f4a6b8754766dafcfa860
出典データセット
uspto-grants-1995_01
特許番号
US05385942

反応ノート

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