Dimethylformamide → Methyl 2-hydroxy-6-(2-methoxy-2-oxoethyl)benzoate

HRID 1583116ノート

反応式

HRID 1583116 の反応式
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:6]=1C(O)=O)([OH:3])=[O:2].[C:15]([O-:18])([O-])=O.[K+].[K+].[CH3:21]I.CN([CH:26]=[O:27])C>>[CH3:15][O:18][C:26](=[O:27])[C:6]1[C:5]([CH2:4][C:1]([O:3][CH3:21])=[O:2])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:14]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 127516562-(Carboxymethyl)-6-hydroxybenzoic acid

生成物 1

HCID 596473Methyl 2-hydroxy-6-(2-methoxy-2-oxoethyl)benzoate収率 56%

反応条件

温度
0 °C

実験手順

To a solution of 2-carboxymethyl-6-hydroxy-benzoic acid (5.021 g, 25.6 mmol) in DMF (100 mL) at 0° C. were added K2CO3(3.567 g, 25.9 mmol) and CH3I (7.9 mL, 51.9 mmol). After stirring under nitrogen at 0° C. for 4 h, the reaction was partitioned between H2O (100 mL) and ether (150 mL). The aqueous layer was acidified with 1 N HCl and extracted with EtOAc (200 mL). The EtOAc layer was dried over MgSO4 and concentrated in vacuo to give the crude 2-hydroxy-6-methoxycarbonylmethyl-benzoic acid methyl ester as a colorless oil (3.2 g, 56%): 1H NMR (CDCl3) δ3.69 (s, 3H), 3.89 (s, 5H), 6.72 (d, J=6.7 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 7.33-7.38 (m, 1H).

後処理

  1. customthe reaction was partitioned between H2O (100 mL) and ether (150 mL)
  2. extractionextracted with EtOAc (200 mL)
  3. dry with materialThe EtOAc layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-94ce4892a21249038abfdfc009e78e96
出典データセット
uspto-grants-2004_05
特許番号
US06740777B2

反応ノート

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