Pyrrolidine → 6-Bromo-3-methyl-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one

HRID 1408730

Reaktionsgleichung

Reaktionsgleichung von HRID 1408730
[Br:1][C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1.[O:13]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]1.N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:19][C:15]1([CH2:16][CH2:17][CH2:18][O:13][CH2:14]1)[CH:9]([CH3:10])[C:8]2=[O:11]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 7364091-(5-Bromo-2-hydroxyphenyl)propan-1-one

Produkt 1

HCID 584240286-Bromo-3-methyl-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-oneAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(5-bromo-2-hydroxyphenyl)propan-1-one (5.7 g, 25 mol), dihydro-2H-pyran-3(4H)-one (5 g, 50 mmol) and pyrrolidine (3.4 g, 48 mmol) in methanol (80 mL) was stirred overnight. The reaction mixture was removed in vacuo, and H2O was added. The resulting solution was extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromo-3-methyl-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (1.2 g, 16%). 1HNMR (CDCl3): 1.16-1.27 (m, 3H), 1.51-1.57 (m, 1H), 1.66-1.73 (m, 1H), 1.91-2.08 (m, 2H), 2.59-2.69 (m, 1H), 3.46-3.56 (m, 2H), 3.88-3.98 (m, 2H), 6.97 (m, 1H), 7.58 (m, 1H), 7.95 (s, 1H).

Aufarbeitung

  1. customThe reaction mixture was removed in vacuo, and H2O
  2. additionwas added
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d0e3ba3219f940008f149451505247c9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921359B2

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