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

HRID 643913노트

반응식

HRID 643913 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1784490421-Butanaminium, N,N,N-tributyl-, (TB-5-11)-difluorotriphenylstannate(1-) (1:1)촉매HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8581758e797349c08c66f4bd4bb9331f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700633B2

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