Trimethylsilylacetylene → 3-(4-Bromophenyl)-5-(trimethylsilyl)isoxazole

HRID 1822938노트

반응식

HRID 1822938 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH:16]=[C:15]([Si:12]([CH3:14])([CH3:13])[CH3:11])[O:8][N:7]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 6080884-Bromobenzaldehyde Oxime

생성물 1

HCID 221704493-(4-Bromophenyl)-5-(trimethylsilyl)isoxazole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

The product from Example 42A (0.124 g, 0.621 mmol) and trimethylsilylacetylene (0.35 mL, 2.5 mmol) were combined in tetrahydrofuran (2.2 mL), treated bleach (2.2 mL), and stirred for 22 hours. The mixture was diluted with ethyl acetate (7 mL), washed with brine (5 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (7% ethyl acetate in hexanes) to provide the title compound.

후처리

  1. additiontreated bleach (2.2 mL)
  2. washwashed with brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (7% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-092d101fbe3d495ba5231d5eafda3b87
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037927B2

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