Methyl iodide → HCID 21923130, compound

HRID 916537Notes

Reaction equation

HRID 916537 reaction equation
[CH3:1][C:2]([N:6]1[Si:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][Si:7]1([CH3:14])[CH3:13])([CH3:5])[C:3]#[CH:4].[CH2:15]([Li])CCC.CI>O1CCCC1>[CH3:5][C:2]([N:6]1[Si:7]([CH3:14])([CH3:13])[CH2:8][CH2:9][Si:10]1([CH3:11])[CH3:12])([CH3:1])[C:3]#[C:4][CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 13389395HCID 13389395, compoundHCID 178418339Butyllithium

Product 1

HCID 21923130HCID 21923130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

The product from Step 1 (13.0 g) in dry tetrahydrofuran (140 ml) was cooled to −70° C. under an atmosphere of nitrogen with stirring and a solution of n-butyl lithium (23.1 ml of 2.5M solution in hexanes) was added at −65 to −70° C. during 5 minutes. The mixture was allowed to warm to −5° C. and methyl iodide (3.93 ml) was added dropwise over 10 minutes. The reaction mixture was allowed to warm to 10° C. when an exothermic reaction occurred. The mixture was maintained at 20° C. by cooling for 2 hours then evaporated under reduced pressure to a small volume. The residue was dissolved in hexane, filtered to remove the insoluble material and evaporated under reduced pressure to give 1-(1,1-dimethyl-2-butynyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane as a yellow oil, 13.0 g.

Workup

  1. temperatureto warm to 10° C. when
  2. customan exothermic reaction
  3. temperatureThe mixture was maintained at 20° C.
  4. temperatureby cooling for 2 hours
  5. customthen evaporated under reduced pressure to a small volume
  6. dissolutionThe residue was dissolved in hexane
  7. filtrationfiltered
  8. customto remove the insoluble material
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-98c396ae90cb440fbb66301caf785cac
Source dataset
uspto-grants-2007_09
Patent number
US07271130B2

Reaction notes

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