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Perchloric Acid → ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-tert-butoxy-acetate

HRID 591023
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Reaktionsgleichung

Reaktionsgleichung von HRID 591023
Cl(O)(=O)(=O)=O.[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:17]([CH:23]([OH:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:18]([CH3:22])[S:19][C:20]=3[CH3:21])=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7]1>C(OC(C)(C)C)(=O)C>[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:17]([CH:23]([O:29][C:10]([CH3:15])([CH3:11])[CH3:9])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:18]([CH3:22])[S:19][C:20]=3[CH3:21])=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7]1
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Komponenten

4

Edukt 2

HCID 24247Perchloric AcidHCID 70855186ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-2-hydroxyacetate

Produkt 1

HCID 70855183ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-tert-butoxy-acetateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10908tert-Butyl acetateLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, perchloric acid (70%, 1.5 mL) was added at −10° C. to a solution of ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-2-hydroxyacetate (17e) (88 mg, 0.25 mmol) in tert-butyl acetate (10 mL). After 1 hour, the reaction was quenched with a saturated aqueous solution of sodium carbonate and extracted with dichloromethane (2×30 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane)) to afford the desired product (17f) as a white solid (43 mg, 0.11 mmol, 43%).

Aufarbeitung

  1. customthe reaction was quenched with a saturated aqueous solution of sodium carbonate
  2. extractionextracted with dichloromethane (2×30 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (dichloromethane))

Quellen und Nachweise

ORD-Eintrag
ord-71d0b71abc144e5896b10b0ed18872c5
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09238026B2

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