Methanol → Methyl 3-methyl-2-benzofurancarboxylate

HRID 2221441

반응식

HRID 2221441 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([OH:13])=[O:12].[C:14](Cl)(=O)C(Cl)=O.CO>CN(C=O)C.C1COCC1>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

참가 물질

6

반응물 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 6005913-Methyl-1-benzofuran-2-carboxylic acid

생성물 1

HCID 74953Methyl 3-methyl-2-benzofurancarboxylate수율 94.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-methyl-benzofuran-2-carboxylic acid (0.98 g, 5.6 mmol) and catalytic amount of DMF (5 drops) in THF (25 ml) was added oxalyl chloride (0.53 ml, 6.1 mmol). After stirring the solution for 1 h at room temperature, methanol (20 ml) and TEA (7.0 ml) were added. The reaction mixture was stirred overnight at room temperature, then concentrated and dissolved in ethyl acetate (100 ml) and washed with aqueous sodium bicarbonate solution (100 ml). The organic layer was dried over sodium sulfate and concentrated to provide crude methyl 3-methylbenzofuran-2-carboxylate (1.0 g, 5.3 mmol) as a tan solid, which was used without further purification.

후처리

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate (100 ml)
  4. washwashed with aqueous sodium bicarbonate solution (100 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c6b527b2c1074afab8ad5326b4ecda9b
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368572B2

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