Potassium Carbonate → 3-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester

HRID 1690469노트

반응식

HRID 1690469 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[S:24][C:25]([CH2:28]Cl)=[CH:26][CH:27]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:28][C:25]2[S:24][C:23]([Cl:22])=[CH:27][CH:26]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 12223651Dimethyl 3-hydroxyphthalate

생성물 1

HCID 669061873-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester수율 99.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.4 g, 6.8 mmol) in acetone (70 mL) and potassium carbonate (2.8 g, 20 mmol) was added 2-chloro-5-chloromethyl-thiophene (0.83 mL, 7.1 mmol) and refluxed for two hours. The solvent was evaporated and the residue was partitioned between water (100 mL) and ethyl acetate (150 mL) and washed with water (2×100 mL). The combined organic phases was dried, concentrated and purified by flash column chromatography (EtOAc/Hexane) to give 3-(5-chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester (2.3 g, 100% crude yield). The product was used in the next step without further purification.

후처리

  1. temperaturerefluxed for two hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water (100 mL) and ethyl acetate (150 mL)
  4. washwashed with water (2×100 mL)
  5. customThe combined organic phases was dried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-921d595929f94738bffdee82f2804321
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153659B2

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