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

HRID 506872

反応式

HRID 506872 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

A stirred mixture of 4.38 g (19.6 mmol) of 1-bromo-naphtalene-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-naphtalene-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.

後処理

  1. customprepared
  2. waitis continued for another hour at 60° C.
  3. customconsumption of 1-bromo-naphtalene-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)

出典と根拠

ORDレコード
ord-a394a736d1e04eec8fc49a65e62e654a
出典データセット
uspto-grants-2010_08
特許番号
US07786123B2

関連ノート

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