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

HRID 25027

반응식

HRID 25027 반응식
[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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b39a908e70c044be99ef9823cba1f34d
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858602B2

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