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

HRID 1583116노트

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HRID 1583116 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-94ce4892a21249038abfdfc009e78e96
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740777B2

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