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

HRID 335624ノート

反応式

HRID 335624 の反応式
[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]

参加物

6

反応物 4

HCID 6356Boron trifluorideHCID 66111TrimethylsilylacetyleneHCID 11008692(R)-tert-Butyldimethyl(oxiran-2-ylmethoxy)silaneHCID 178418306HCID 178418306、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a71f18db6a384052bd2c43e84030d6b8
出典データセット
uspto-grants-2014_11
特許番号
US08884058B2

反応ノート

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