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Water → 6-morpholino-3,4-dihydronaphthalen-1(2H)-one

HRID 1446602
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1446602
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(OCC)(=O)C>[N:20]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]3)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1
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Komponenten

9

Edukt 4

HCID 962WaterHCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Produkt 1

HCID 131795016-morpholino-3,4-dihydronaphthalen-1(2H)-oneAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2734215
2-(Di-tert-butylphosphino)biphenyl
Katalysator
HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysator
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (3.40 g), morpholine (5.18 g), tripotassium phosphate (3.79 g), tris(dibenzylideneacetone) dipalladium (0) (109 mg) and 2-(di-tert-butylphosphino)biphenyl (71 mg) in 1,2-dimethoxyethane (24 mL) was stirred in a nitrogen atmosphere at 80° C. for one and a half hours. The reaction solution was returned to room temperature, and water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent:heptane-ethyl acetate system) to obtain 2.56 g of the title compound. Properties data of the compound are as follows.

Aufarbeitung

  1. customwas returned to room temperature
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (elution solvent:heptane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-b1180be557c1415fb6a977be0f358bda
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07667041B2

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