Dimethylformamide → 2,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde

HRID 1798058ノート

反応式

HRID 1798058 の反応式
Br[C:2]1[C:7]([CH2:8][O:9][CH3:10])=[CH:6][C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]=1[O:15][CH2:16][O:17][CH3:18].[Li]CCCC.CN([CH:27]=[O:28])C>CCOCC>[CH3:18][O:17][CH2:16][O:15][C:3]1[CH:4]=[C:5]([O:11][CH2:12][O:13][CH3:14])[CH:6]=[C:7]([CH2:8][O:9][CH3:10])[C:2]=1[CH:27]=[O:28]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 582927852-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzeneHCID 178418339Butyllithium

生成物 1

HCID 582925712,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde収率 82.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (5.66 g, 17.59 mmol) in Et2O (60 mL) was added n-BuLi (15.47 mL, 2.5 M in Hexane) at −78° C. After stirring for 1 hour at −78° C., DMF (13.6 mL, 175.8 mmol) was the added and reaction mixture was allowed to warm to room temperature over 3 hours. The reaction was quenched with saturated NH4Cl and extracted with Et2O. The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2,4-bis-methoxymethoxy-6-methoxymethyl-benzaldehyde (3.93 g, 82%). 1H NMR (400 MHz, CDCl3δ 10.50 (s, 1H), 7.03 (s, 1H), 6.77 (s, 1H), 5.30 (s, 2H), 5.27 (s, 2H), 4.80 (s, 3H), 3.50 (s, 3H), 4.49 (s, 3H).

後処理

  1. additionadded
  2. customreaction mixture
  3. temperatureto warm to room temperature over 3 hours
  4. customThe reaction was quenched with saturated NH4Cl
  5. extractionextracted with Et2O
  6. customThe organic extracts were dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-2ffb4afab5834de892ca0971f1354952
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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