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

HRID 984506

反応式

HRID 984506 の反応式
[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]

参加物

5

反応物 3

HCID 123501-HeptyneHCID 137554Silacyclobutane, 1-chloro-1-methyl-HCID 178418348HCID 178418348、化合物

生成物 1

HCID 99423051-Methyl-(1-heptynyl)silacyclobutane収率 92%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-a1c0d22ab7b548cc9a9e2f4f55190fe0
出典データセット
uspto-grants-2005_03
特許番号
US06867323B2

関連ノート

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