5-(Trifluoromethyl)-5H-dibenzo[B,D]thiophen-5-ium tetrafluoroborate → 6-Methoxy-2-trifluoromethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 643913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643913
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][Si](C)(C)C)=[CH:8][CH2:7][CH2:6]2.F[B-](F)(F)F.[F:23][C:24]([F:39])([F:38])[S+]1C2C=CC=CC=2C2C=CC=CC1=2>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.C1C=CC([Sn-](F)(F)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([C:24]([F:39])([F:38])[F:23])[CH2:7][CH2:6]2

Komponenten

5

Edukt 2

HCID 27775045-(Trifluoromethyl)-5H-dibenzo[B,D]thiophen-5-ium tetrafluoroborateHCID 12705557(6-Methoxy-3,4-dihydronaphthalen-1-yloxy)-trimethylsilane

Produkt 1

HCID 534070246-Methoxy-2-trifluoromethyl-3,4-dihydro-2H-naphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1784490421-Butanaminium, N,N,N-tributyl-, (TB-5-11)-difluorotriphenylstannate(1-) (1:1)KatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of (6-methoxy-3,4-dihydronaphthalen-1-yloxy)-trimethylsilane (3.00 g, from step A) and 5-trifluoromethyldibenzothiophenium tetrafluoroborate (5.6 g, 16.5 mmol) in DMF (20 mL) is added slowly tetrabutylammonium difluorotriphenylstannate (7.0 g, 11.1 mmol) in DMF (40 mL) by a dropping funnel. After the addition is finished, the suspension is stirred at RT for 72 h. DMF is then removed under vacuum. Water and EtOAc are added. The organic layer is dried with MgSO4, concentrated and purified to give the title compound as a light yellow oil: 1H NMR (CDCl3) δ 2.24-2.31 (m, 1H), 2.44-2.50 (m, 1H), 3.01-3.07 (m, 2H), 3.20-3.25 (m, 1H), 3.87 (s, 3H), 6.70 (d, J=2.5 Hz, 1H), 6.86 (dd, J=2.52, 9 Hz, 1H), 8.04 (d, J=9 Hz, 1H).

Aufarbeitung

  1. additionAfter the addition
  2. customDMF is then removed under vacuum
  3. additionWater and EtOAc are added
  4. dry with materialThe organic layer is dried with MgSO4
  5. concentrationconcentrated
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-8581758e797349c08c66f4bd4bb9331f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700633B2

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