Allylchlorodimethylsilane → Allyldimethyl-[4-(terahydropyran-2-yloxy)-but-1-ynyl]-silane

HRID 1582517

반응식

HRID 1582517 반응식
C([Li])CCC.[CH2:6]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:7][CH:8]=[CH2:9].[CH2:17]([Si:20](Cl)([CH3:22])[CH3:21])[CH:18]=[CH2:19]>C1COCC1>[CH2:17]([Si:20]([CH3:22])([CH3:21])[C:9]#[C:8][CH2:7][CH2:6][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:18]=[CH2:19]

참가 물질

5

반응물 3

HCID 77646AllylchlorodimethylsilaneHCID 3199452-But-3-enoxyoxaneHCID 178418339Butyllithium

생성물 1

HCID 20726336Allyldimethyl-[4-(terahydropyran-2-yloxy)-but-1-ynyl]-silane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of n-butyllithium (12.0 ml, 30 mmol, 2.5 mol dm−3 in hexanes) was added dropwise to a stirred, cooled (−78° C.) solution of compound 2 (4.62 g, 30 mmol) in THF (60 ml) under an atmosphere of dry nitrogen. The reaction mixture was maintained at −78° C. for 1.5 h and a solution of allylchlorodimethylsilane (4.04 g, 30 mmol) in THF (20 ml) added dropwise. The reaction mixture was allowed to warm to room temperature, washed with water and the organic layer extracted into ethyl acetate/hexane (3 times). The combined extracts were washed with brine, dried (MgSO4) and the solvent removed in vacuo to yield a clear oil. The crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.48]

후처리

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. extractionthe organic layer extracted into ethyl acetate/hexane (3 times)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto yield a clear oil
  8. customThe crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.48]

출처 및 근거

ORD 기록
ord-a225dab37c6a49c692f2e9f0403b1aeb
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737124B2

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