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Chlorotrimethylsilane → HCID 14774099, 화합물

HRID 2073819
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인쇄 미리보기

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HRID 2073819 반응식
C(NC(C)C)(C)C.C([Li])CCC.[Li+].CC([N-]C(C)C)C.[F:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[C:30]1[O:31][CH2:32][C:33]([CH3:36])([CH3:35])[N:34]=1.Cl[Si:38]([CH3:41])([CH3:40])[CH3:39]>C1COCC1.O>[F:21][C:22]1[C:27]([Si:38]([CH3:41])([CH3:40])[CH3:39])=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[C:30]1[O:31][CH2:32][C:33]([CH3:36])([CH3:35])[N:34]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 110097342-(2,4,5-Trifluorophenyl)-4,5-dihydro-4,4-dimethyloxazoleHCID 178418339Butyllithium

생성물 1

HCID 14774099HCID 14774099, 화합물수율 83.1%

시약·촉매·용매

2
HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of 8.7 ml (62.1 mmol) of diisopropylamine in 100 ml of dry THF under argon was cooled to -78° C. and treated with 28.3 ml (56.6 mmol) of 2.0M n-butyllithium. The LDA solution was stirred at -78° C. for 15 minutes. To this solution was added a solution of 11.8 g (51.5 mmol) of 2-(2,4,5-trifluorophenyl)-4,4-dimethyl-2-oxazoline in 50 ml of THF, and the reaction mixture was stirred for one hour at -78° C. To the reaction mixture was added 13 ml (102.5 mmol) of chlorotrimethylsilane, and the solution was warmed to room temperature. Water was added; the organic layer was dried over magnesium sulfate and concentrated. The crude product was chromatographed on silica gel (E. Merck 230-400 Mesh), eluting with 80:20 chloroform:ethyl acetate to give 12.9 g of the title compound, mp 71°-72° C.

후처리

  1. temperaturethe solution was warmed to room temperature
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (E. Merck 230-400 Mesh)
  5. washeluting with 80:20 chloroform

출처 및 근거

ORD 기록
ord-41f8b95ddabe44c497e519919f4c0c7c
출처 데이터셋
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04920120

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