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Methyl (trimethylsilyl)acetate → Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

HRID 2375742
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HRID 2375742 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si]([CH2:15][C:16]([O:18][CH3:19])=[O:17])(C)C.[O:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)=[CH:29][CH:28]=1)=O>C1COCC1>[O:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)=[CH:31][CH:32]=1)=[CH:15][C:16]([O:18][CH3:19])=[O:17]
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참가 물질

5

반응물 3

HCID 76210Methyl (trimethylsilyl)acetateHCID 2733832Lithium hexamethyldisilazaneHCID 59855138Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

생성물 1

HCID 69142498Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Lithium bis(trimethylsilyl)amide (3.46 mmol, 1M in THF) was added dropwise to a solution of methyl trimethylsilylacetate (3.46 mmol) in THF (5 mL) at −78° C. After 20 minutes at −78° C., a solution of 10.2 (2.16 mmol) in THF (9 mL) was added dropwise and the reaction was maintained at −78° C. for 1.5 hours. The reaction was quenched with water and extracted with EtOAc. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (silica gel, 1:1 EtOAc/hexane) to afford compound 10.3. MS ESI (pos.) m/e 330.1 (M+1).

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel, 1:1 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-9c43854d0d8344388626969d8e98f312
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07465804B2

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