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

HRID 643913Notes

Reaction equation

HRID 643913 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1784490421-Butanaminium, N,N,N-tributyl-, (TB-5-11)-difluorotriphenylstannate(1-) (1:1)CatalystHCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8581758e797349c08c66f4bd4bb9331f
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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