Ethyl Acetate → 2-[3-(2-{[Tert-butyl(dimethyl)silyl]oxy}-ethoxy)-4-methylphenyl]-1,3-benzoxazole

HRID 7717

반응식

HRID 7717 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([CH3:17])=[C:14]([OH:16])[CH:15]=1.[H-].[Na+].Br[CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCOC(C)=O>CN(C=O)C>[Si:24]([O:23][CH2:22][CH2:21][O:16][C:14]1[CH:15]=[C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH:11]=[CH:12][C:13]=1[CH3:17])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 219910005-(1,3-Benzoxazol-2-yl)-2-methylphenol

생성물 1

HCID 695846442-[3-(2-{[Tert-butyl(dimethyl)silyl]oxy}-ethoxy)-4-methylphenyl]-1,3-benzoxazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (355 mg, 1.6 mmol) in DMF (10 mL) was cooled to 0° C. and NaH (70 mg, 1.7 mmol) was added slowly. After 15 min, (2-bromoethoxy)(tert-butyl)dimethylsilane (370 μL, 1.7 mmol) was added. The reaction was then elevated to 90° C. for 1 h and EtOAc (100 mL) was added. The EtOAc solution was washed with brine (3×20 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash column (silica gel, hexanes:EtOAc 1:5) to afford 2-[3-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethoxy)-4-methylphenyl]-1,3-benzoxazole.

후처리

  1. waitThe reaction was then elevated to 90° C. for 1 h
  2. washThe EtOAc solution was washed with brine (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column (silica gel, hexanes:EtOAc 1:5)

출처 및 근거

ORD 기록
ord-b17d33ee2364483d9d7165289ffaf585
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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