Acetic Acid → diethyl 6-acetyl-3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

HRID 2371652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371652
[CH2:1]([C:4]1[C:13]2[O:12][C:11]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[OH:28])[CH2:2][CH3:3].[C:29](O)(=[O:31])[CH3:30]>[Cl-].[Zn+2].[Cl-]>[C:29]([C:6]1[C:5]([OH:28])=[C:4]([CH2:1][CH2:2][CH3:3])[C:13]2[O:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][CH2:9][C:8]=2[CH:7]=1)(=[O:31])[CH3:30]

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 15157486diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

Produkt 1

HCID 15157494diethyl 6-acetyl-3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

To a solution of 790 mg (2.01 mmol) of the title product of Example 44 in 4 ml of acetic acid was added 547 mg (4.02 mmol) of anhydrous zinc chloride. The mixture was stirred for six hours at reflux, and then permitted to cool. The mixture was partitioned between ethyl acetate and dilute hydrochloric acid. The aqueous layer was further extracted with two portions of ethyl acetate. The combined organic extracts were washed successively with five portions of aqueous sodium bicarbonate, water, and then brine. The extracts were dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. Chromatography of the residue over silica gel using 25% ethyl acetate/hexane as eluent gave the title compound, 230 mg.

Aufarbeitung

  1. temperatureat reflux
  2. temperatureto cool
  3. customThe mixture was partitioned between ethyl acetate and dilute hydrochloric acid
  4. extractionThe aqueous layer was further extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed successively with five portions of aqueous sodium bicarbonate, water
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-843ce68f4a4c4bccb551b0af42613444
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05093353

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