Dimethylformamide → Ethyl 6-methoxybenzo[b]thiophene-2-carboxylate

HRID 1171227

反応式

HRID 1171227 の反応式
CN(C)C=O.F[C:7]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:8]=1[CH:9]=O.[SH:17][CH2:18][C:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].[C:28](OCC)(=O)[CH3:29]>O>[CH2:28]([O:20][C:19]([C:18]1[S:17][C:7]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:8]=2[CH:9]=1)=[O:21])[CH3:29]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27348732-Fluoro-4-methoxybenzaldehydeHCID 5086465Acetic acid, mercapto-, ion(1-)

生成物 1

HCID 11831419Ethyl 6-methoxybenzo[b]thiophene-2-carboxylate収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an N,N-dimethylformamide (50 mL) solution of 2-fluoro-4-methoxybenzaldehyde (5.0 g, 32.5 mmol) and 2-mercapto-acetate (3.56 mL, 32.5 mmol) was added potassium carbonate (12.1 g, 87.5 mmol). This mixture was stirred at room temperature for 5 hours. The reaction mixture was distributed between ethyl acetate and water. The organic layer was separated followed by washing with water, drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1 to 10:1) and NH silica gel chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (6.72 g, 88%).

後処理

  1. customThe organic layer was separated
  2. washby washing with water
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe resulting residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1 to 10:1) and NH silica gel chromatography (heptane:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-4e097e1663ab4403856981b799d8f174
出典データセット
uspto-grants-2010_11
特許番号
US07829585B2

関連ノート

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