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

HRID 1171227

반응식

HRID 1171227 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4e097e1663ab4403856981b799d8f174
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829585B2

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