Reaction #470409

ord-4447b5e2032b404f84f2158865148544

Reaction equation

[Li][CH2]CCC
BuLi
C[Si](C)(C)N[Si](C)(C)C
hexamethyldisilazane
[Cl-].[NH4+]
NH4Cl
C[Si](C)(C)[N-][Si](C)(C)C.[Li+]
lithiumhexamethyl disilazide

Conditions

Temperature
-40°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGThe mixture subsequently stirred at −70° C. for an additional hr
  2. 2
    Extractionextracted with ethyl acetate

Procedure

A solution of lithiumhexamethyl disilazide was prepared by adding 4.8 ml of 1.6 m BuLi in hexanes to a solution of 1.8 ml of hexamethyldisilazane in 10 ml of dry THF at −40° C. This solution was stirred for 15 min at −40° C. A quantity of 7.8 ml of this solution was added dropwise to a solution of 1.34 g of compound 13 in 20 ml of dry THF at −70° C. The mixture subsequently stirred at −70° C. for an additional hr and then poured into 50 ml of sat. NH4Cl solution and extracted with ethyl acetate.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08367648B2uspto-grants-2013_02