Sodium, 2,4-cyclopentadien-1-yl- → HCID 131724107, compound

HRID 988863Notes

Reaction equation

HRID 988863 reaction equation
[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Na+].Br[CH2:8][Si:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10]>O1CCCC1>[C:13]([NH:12][Si:9]([CH3:11])([CH3:10])[CH2:8][CH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 78681Sodium, 2,4-cyclopentadien-1-yl-HCID 180000441-(bromomethyl)-N-(1,1-dimethylethyl)-1,1-dimethylsilanamine

Product 1

HCID 131724107HCID 131724107, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

32.7 ml of a 2.3 M solution (75 mmol) of sodium cyclopentadienide in tetrahydrofurane was added to a solution of 11.4 g (51 mmol) of 2-bromo-1-tertbutylamino-1,1-dimethylsilaethane. The immediate formation of a pinkish solid was observed, the reaction was continued for 8 hours, then it was concentrated to dryness and it was extracted with hexane, the resulting solution was evaporated in order to give a yellow oil, that corresponds to a mixture of isomers (12.5 g, 60 mmol, yield: 80%). 1H-NMR (CDCl3): 6.5-5.75(m,3H), 2.95(m,2H), 1.90(m,2H), 1.20(s,9H), 0.10(s,6H).

Workup

  1. concentrationit was concentrated to dryness and it
  2. extractionwas extracted with hexane
  3. customthe resulting solution was evaporated in order
  4. customto give a yellow oil
  5. additionthat corresponds to a mixture of isomers (12.5 g, 60 mmol, yield: 80%)

Sources & evidence

ORD record
ord-4637cb414d054494a394713a73ebbfa6
Source dataset
uspto-grants-2003_10
Patent number
US06635778B1

Reaction notes

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