Water → 1-(3-Chloropropyl)-3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran

HRID 223234

Reaktionsgleichung

Reaktionsgleichung von HRID 223234
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1O[C:17]([CH2:19][CH2:20][CH2:21][Cl:22])([CH3:18])OC1.B(F)(F)F.O>[N+](C)([O-])=O>[Cl:22][CH2:21][CH2:20][CH2:19][C:17]1([CH3:18])[C:6]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=2)[CH2:11][CH2:12][O:13]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6356Boron trifluorideHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 819113,4-Dimethoxyphenethyl alcohol

Produkt 1

HCID 130157811-(3-Chloropropyl)-3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyranAusbeute 1.404,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6375NitromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3,4-dimethoxyphenylethyl alcohol (1.72 g, 0.01 mole), 5-chloro-2-pentanone ethylene ketal (1.64 g, 0.01 mole) and 0.5 ml of BF3 etherate in 20 ml of nitromethane is stirred at room temperature under N2 for 4 hours. The reaction mixture is then poured into cold water and extracted with CH2Cl2. The CH2Cl2 solution is washed with water, dried (Na2SO4) and concentrated to an oil. The oil is chromatographed on silica gel with 10% ethylacetate/Skellysolve B as eluate to give 40 g (54% yield) of 1-(3-chloropropyl)-6,7-dimethoxy-1-methyl-isochroman as a white crystalline product, m.p. 77°-79° C. The nmr of the product is consistent with the structure.

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. washThe CH2Cl2 solution is washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel with 10% ethylacetate/Skellysolve B as eluate

Quellen und Nachweise

ORD-Eintrag
ord-167e8c751d4c4ce6bf8823565b4bbbe9
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04352805

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