Boron trifluoride → (R)-1-((tert-Butyldimethylsilyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

HRID 929452노트

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HRID 929452 반응식
[Li]C(C)(C)C.[Si:6]([C:10]#[CH:11])([CH3:9])([CH3:8])[CH3:7].[C:12]([Si:16]([CH3:23])([CH3:22])[O:17][CH2:18][C@H:19]1[CH2:21][O:20]1)([CH3:15])([CH3:14])[CH3:13].B(F)(F)F>C1COCC1>[Si:16]([O:17][CH2:18][C@H:19]([OH:20])[CH2:21][C:11]#[C:10][Si:6]([CH3:9])([CH3:8])[CH3:7])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:23])[CH3:22]

참가 물질

6

반응물 4

HCID 6356Boron trifluorideHCID 66111TrimethylsilylacetyleneHCID 11008692(R)-tert-Butyldimethyl(oxiran-2-ylmethoxy)silaneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 53308767(R)-1-((tert-Butyldimethylsilyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

tert-BuLi (12.4 ml, 1.7M, 21.1 mmol) was added to a solution of TMS-acetylene (2.12 g, 21.7 mmol) in THF (40 ml) at −78° C. and the reaction mixture was stirred for an additional 30 min. (R)-tert-butyldimethyl(oxiran-2-ylmethoxy)silane (2 g, 10.6 mmol) and BF3.EtO2 (3 g, 21.1 mmol) were added and stirred at −78° C. for 4.5 hours. The reaction was then quenched by addition of aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure to afford the desired material in a quantitative yield. The material was used in the next step with no further purification.

후처리

  1. additionEtO2 (3 g, 21.1 mmol) were added
  2. customThe reaction was then quenched by addition of aqueous ammonium chloride solution
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1a0c91ab7f6a410d8b89026e6486b347
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296686B2

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