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

HRID 1915174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915174
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 669061873-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl esterAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-07d0745e045846d583d6113a8341d2bc
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614328B2

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