Methanesulfonic Acid → HCID 66766901, Verbindung

HRID 2195505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2195505
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:7][N:6]=[CH:5]2.CS(O)(=O)=O.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl.C1COCC1>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:7]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1)[N:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 66766802Ethyl 5-hydroxy-1H-indazole-6-carboxylate

Produkt 1

HCID 66766901HCID 66766901, VerbindungAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 5-hydroxy-1H-indazole-6-carboxylate (15.5 g, 75 mmol) in DCM (100 mL) and THF (100 mL) containing methanesulfonic acid (721 mg, 7.5 mmol) is added a solution of 3,4-dihydro-2H-pyran (6.6 g, 79 mmol) in DCM (20 mL) dropwise at RT. The resulting solution is stirred at RT overnight. After the solvent is removed, EtOAc (500 mL), saturated aqueous sodium chloride (500 mL) and NaHCO3 (5 g) are added. The organic layer is separated, dried and concentrated. The residue is purified by silica gel column chromatography to afford the product (16.8 g, 77% yield). MS (m/z): 291.1 (M+H).

Aufarbeitung

  1. customAfter the solvent is removed
  2. additionEtOAc (500 mL), saturated aqueous sodium chloride (500 mL) and NaHCO3 (5 g) are added
  3. customThe organic layer is separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-59db8290479847ba9958bc6270251dbd
Quelldatensatz
uspto-grants-2012_12
Patentnummer
USRE043878E1

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