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

HRID 984506

Reaction equation

HRID 984506 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-a1c0d22ab7b548cc9a9e2f4f55190fe0
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Linked notes

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