4-Methylmorpholine → 5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

HRID 32073

Reaktionsgleichung

Reaktionsgleichung von HRID 32073
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[CH2:22][CH2:21][CH2:20]2.CN1CCOCC1.[NH4+].[Cl-]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:27]=[C:23]1[CH2:22][CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:26]=[CH:25][C:24]1=2

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Produkt 1

HCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trifluoro-methanesulfonic anhydride (14.35 mL, 77.3 mmol) was added to a CH2Cl2 (150 mL) solution of 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (11.40 g, 70.3 mmol), N-methylmorpholine (8.5 mL, 77.3 mmol) and DMAP (130 mg, 1 mmol) in 5 min at −80° C. The mixture was warmed to 0° C. in 1 h then poured into a cold solution of saturated NH4Cl. The mixture was diluted with CH2Cl2 (400 mL), washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo to provide the crude compound which was purified by column chromatography (silica, 0 to 60% CH2Cl2 in hexane) to provide the title compound.

Aufarbeitung

  1. washwashed with H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide the crude compound which
  6. customwas purified by column chromatography (silica, 0 to 60% CH2Cl2 in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3b582824b37743d5aefae7d5d204232e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425631B2

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