2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 4,4,5,5-Tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane

HRID 601456

반응식

HRID 601456 반응식
[Li]CCCC.I[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1.C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>C1COCC1>[CH3:32][C:27]1([CH3:33])[C:28]([CH3:31])([CH3:30])[O:29][B:25]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=2)[O:26]1

참가 물질

5

반응물 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 115948361-Iodo-4-octylbenzeneHCID 178418339Butyllithium

생성물 1

HCID 588233864,4,5,5-Tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

n-BuLi (16.6 mL, 1.6 M in hexanes) was added over 10 minutes to a solution of 1-iodo-4-octylbenzene from Part A (6.9 g, 21.8 mmol) in dry THF (100 mL) at −78° C. under a nitrogen atmosphere. The mixture was stirred for another 10 minutes at −78° C. 2-Isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (6.21 mL, 30.4 mmol) was subsequently added dropwise to the mixture and stirring was continued at room temperature overnight. The reaction was then quenched with distilled water, and THF was removed under vacuum. The product was then extracted into diethyl ether and the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo to give 6.38 g of 4,4,5,5-tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane as a colorless oil. The product was used in the next step without further purification.

후처리

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customThe reaction was then quenched with distilled water, and THF
  4. customwas removed under vacuum
  5. extractionThe product was then extracted into diethyl ether
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-e2477bd9e1ec49968840cad319376436
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902363B2

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