Potassium Carbonate → 1-Bromo-3-(2-triisopropylsilyloxy-ethoxy)-naphtalene

HRID 1352722

반응식

HRID 1352722 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.Br[CH2:14][CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:12][CH2:14][CH2:15][O:16][Si:17]([CH:21]([CH3:22])[CH3:23])([CH:18]([CH3:20])[CH3:19])[CH:24]([CH3:25])[CH3:26])[CH:3]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 121155964-Bromo-2-naphtholHCID 12137438Silane, (2-bromoethoxy)tris(1-methylethyl)-2회

생성물 1

HCID 121155971-Bromo-3-(2-triisopropylsilyloxy-ethoxy)-naphtalene

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

A stirred mixture of 4.38 g (19.6 mmol) of 1-bromo-naphtalen-3-ol (prepared according to the procedure of M. S. Newman, V. Sankaran, D. R. Olson, J. Am. Chem. Soc. 1976, 98, 3237–3242), 5.52 g (19.6 mmol) of 1-bromo-2-triisopropylsilyloxy-ethane, 13.56 g (98.1 mmol) of potassium carbonate and 1.45 g (3.9 mmol) of tetrabutylammonium iodide in 50 mL of dimethylformamide is heated to 60° C. for 4 hours. Then an additional 0.55 g (2.0 mmol) of 1-bromo-2-triisopropylsilyloxy-ethane are added and stirring is continued for another hour at 60° C., after which TLC analysis indicated complete consumption of 1-bromo-naphtalen-3-ol. The mixture is allowed to cool to room temperature and brine is added. The resulting solution is extracted with ethyl acetate. The organic solution is washed twice with brine and the combined aqueous layers are back extracted with ethyl acetate. The organic layers are combined, dried, filtered and concentrated under reduced pressure. The oily brown residue is purified by column chromatography on silica gel (97.5:2.5 n-hexane/diethylether) to afford above title compound as a brown solid.

후처리

  1. customprepared
  2. waitis continued for another hour at 60° C.
  3. customconsumption of 1-bromo-naphtalen-3-ol
  4. additionbrine is added
  5. extractionThe resulting solution is extracted with ethyl acetate
  6. washThe organic solution is washed twice with brine
  7. extractionthe combined aqueous layers are back extracted with ethyl acetate
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe oily brown residue is purified by column chromatography on silica gel (97.5:2.5 n-hexane/diethylether)

출처 및 근거

ORD 기록
ord-4b0dad2faa5847a19ec25e20aa25fd92
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220774B2

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