Dimethylformamide → Methyl 5-formyl-2-methylfuran-3-carboxylate

HRID 68572

反応式

HRID 68572 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]([C:10]1[CH:14]=[CH:13][O:12][C:11]=1[CH3:15])=[O:9].[OH-].[Na+].CN([CH:21]=[O:22])C>>[CH3:6][O:7][C:8]([C:10]1[CH:14]=[C:13]([CH:21]=[O:22])[O:12][C:11]=1[CH3:15])=[O:9]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 80237Methyl 2-methylfuran-3-carboxylate

生成物 1

HCID 2779820Methyl 5-formyl-2-methylfuran-3-carboxylate

実験手順

Phosphorus oxychloride (33 ml) is added dropwise to a solution of 2-methyl-furan-3-carboxylic acid methyl ester (25.0 g) in DMF (75 ml) under nitrogen at 0° C. After 3 h 30 at 40° C., the reaction mixture is slowly poured onto water at 0° C. and NaOH 5 N is added carefully. The mixture is extracted three times with diethyl ether. The combined organic phases are washed with a saturated aqueous solution of NaHCO3, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by chromatography on silica gel eluting with a mixture of diethyl ether and ethyl acetate (3:1) to yield 5-formyl-2-methyl-furan-3-carboxylic acid methyl ester (22.36 g) as a yellow solid. MS (HPLC/MS): 169 (MH+).

後処理

  1. additionthe reaction mixture is slowly poured onto water at 0° C.
  2. extractionThe mixture is extracted three times with diethyl ether
  3. washThe combined organic phases are washed with a saturated aqueous solution of NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by chromatography on silica gel eluting with a mixture of diethyl ether and ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-f542d4908c674ae4bded20803a914ca4
出典データセット
uspto-grants-2014_09
特許番号
US08822466B2

関連ノート

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