1-Heptyne → 1-Methyl-(1-heptynyl)silacyclobutane

HRID 984506

반응식

HRID 984506 반응식
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Li]C.Cl[Si:11]1([CH3:15])[CH2:14][CH2:13][CH2:12]1>CCOCC>[C:1]([Si:11]1([CH3:15])[CH2:14][CH2:13][CH2:12]1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

참가 물질

5

반응물 3

HCID 123501-HeptyneHCID 137554Silacyclobutane, 1-chloro-1-methyl-HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 99423051-Methyl-(1-heptynyl)silacyclobutane수율 92%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 1-heptyne (1.31 mL, d=0.7238, 0.960 g, 10.0 mmol) in Et2O (10 mL) was added a solution of MeLi (9.43 mL, 1.06 M in Et2O, 1.0 equiv) at −78° C. After being stirred for 3 h, 1-chloro-1-methylsilacyclobutane (1.16 mL, 1.0 equiv) was added dropwise to the reaction solution at the same temperature, which was then stirred for another 5 h. The reaction mixture was quenched with H2O (10 mL) and then was extracted with pentane (3×25 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford the crude product, which was purified by column chromatography (SiO2, pentane) and Kugelrohr distillation to afford 1.66 g (92%) of 1-(1heptynyl)-1-methylsilacyclobutane as colorless oil

후처리

  1. stirringwas then stirred for another 5 h
  2. customThe reaction mixture was quenched with H2O (10 mL)
  3. extractionwas extracted with pentane (3×25 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product, which
  7. distillationwas purified by column chromatography (SiO2, pentane) and Kugelrohr distillation

출처 및 근거

ORD 기록
ord-a1c0d22ab7b548cc9a9e2f4f55190fe0
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867323B2

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