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Methanol → 2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde

HRID 505661
ノート
印刷プレビュー

反応式

HRID 505661 の反応式
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)[CH:27]=[O:28].O.CO>C(OCC)C>[CH2:18]([O:17][CH2:16][C:3]1[CH:4]=[C:5]([O:12][CH2:13][O:14][CH3:15])[CH:6]=[C:7]([O:8][CH2:9][O:10][CH3:11])[C:2]=1[CH:27]=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 6228DimethylformamideHCID 231475942-Bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene

生成物 1

HCID 216698172-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde収率 72%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether
溶媒

反応条件

温度
-78 °C

実験手順

The above-obtained 2-bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene (1.6 g, 4.3 mmol) was dissolved in diethylether (25 mL) and cooled to −78° C. The obtained solution was added with 1.52 mol/L n-butyllithium-hexane solution (4.0 mL, 6.1 mmol) and stirred at −78° C. for 1 hour. Then, N,N-dimethylformamide (1.0 mL, 13 mmol) was added thereto and stirred at a room temperature for 3 hours. The reaction mixture was added with water and methanol, and then extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, and then dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 to 5/1 to 3/1) to obtain 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde (0.99 g, 72%).

後処理

  1. additionThe obtained solution was added with 1.52 mol/L n-butyllithium-hexane solution (4.0 mL, 6.1 mmol)
  2. stirringstirred at a room temperature for 3 hours
  3. extractionextracted with chloroform 3 times
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThen the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 to 5/1 to 3/1)

出典と根拠

ORDレコード
ord-4f6fedc485ba409ca1005d609e123232
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07781485B2

反応ノート

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