Hydrochloric Acid → 4,4,5,5-Tetramethyl-2-(pent-1-yn-1-yl)-1,3,2-dioxaborolane

HRID 629842

反応式

HRID 629842 の反応式
[Li][CH2:2][CH2:3][CH2:4][CH3:5].C(O[B:10]1[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]1)(C)C.[C-:19]#[C-].[Li+].[Li+].Cl>C1COCC1>[CH3:16][C:13]1([CH3:15])[C:12]([CH3:17])([CH3:18])[O:11][B:10]([C:5]#[C:4][CH2:3][CH2:2][CH3:19])[O:14]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418339ButyllithiumHCID 178462446HCID 178462446、化合物

生成物 1

HCID 467390524,4,5,5-Tetramethyl-2-(pent-1-yn-1-yl)-1,3,2-dioxaborolane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a stirred solution of IIc′ (5 mL, 51 mmol) in dry THF (25 mL) at −78° C. was added n-BuLi (2.5 M in n-hexane, 22.4 mL, 56 mmol). Another flask was charged with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.4 mL, 51 mmol) in dry THF (50 mL) under argon atmosphere, and the reaction mixture was cooled to −78° C. The lithium acetylide from the first flask, which was cooled to −78° C., was slowly added to the second by a double-ended needle. The mixture was stirred at −78° C. for 2 hours, after which anhydrous HCl (56 mmol) was added. Then, reaction mixture was warmed to room temperature. After removal of the precipitated LiCl by filtration and removal of solvents under reduced pressure, the residue was purified by distillation (115-125° C./15 mbar) to afford IIIc (6.3 g, 64%) as an oil.

後処理

  1. additionwas slowly added to the second by a double-ended needle
  2. customThen, reaction mixture
  3. temperaturewas warmed to room temperature
  4. customAfter removal of the precipitated LiCl
  5. filtrationby filtration and removal of solvents under reduced pressure
  6. distillationthe residue was purified by distillation (115-125° C./15 mbar)
  7. customto afford IIIc (6.3 g, 64%) as an oil

出典と根拠

ORDレコード
ord-bac880f817314b8eb32bbd61582245a7
出典データセット
uspto-grants-2016_04
特許番号
US09315525B2

関連ノート

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