Chlorotrimethylsilane → N-(2,6-Dimethylbenzyl)phthalimide

HRID 25027

反応式

HRID 25027 の反応式
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4]O.Cl[Si](C)(C)C.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CS(C)=O.CN(C=O)C.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][N:20]1[C:16](=[O:26])[C:17]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:18]2[C:19]1=[O:21]

参加物

8

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 186748(2,6-Dimethylphenyl)methanolHCID 24194345Phthalimide potassium salt

生成物 1

HCID 10825581N-(2,6-Dimethylbenzyl)phthalimide

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a stirred solution of 2,6-Dimethylbenzyl Alcohol (Step A, 6.59 g, 48.4 mmol) in DMSO (20 ml) was added chlorotrimethylsilane (15.75 ml, 145 mmol) at room temperature, and the mixture was stirred for one hr. To this reaction mixture were added ethyl acetate and water, the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give an oil. The oily residue was redissolved in DMF (100 ml) and potassium phthalimide (10.76 g, 58.1 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature, ethyl acetate was added, and the organic layer was washed with 3% Na2CO3, 1 N HCl, dried over Na2SO4, filtered and concentrated to give white solid. The purification was done by flash chromatography on silica gel column (chloroform:methanol 95:5) to provide the title compound as white solid.

後処理

  1. washthe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an oil
  6. stirringThe reaction mixture was stirred for 16 hours at room temperature
  7. washthe organic layer was washed with 3% Na2CO3, 1 N HCl
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give white solid
  12. customThe purification

出典と根拠

ORDレコード
ord-b39a908e70c044be99ef9823cba1f34d
出典データセット
uspto-grants-2005_02
特許番号
US06858602B2

関連ノート

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