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

HRID 629842

반응식

HRID 629842 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bac880f817314b8eb32bbd61582245a7
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315525B2

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