Ammonium Chloride → (3-Trimethylsiloxypropyl)-cyclopentadiene

HRID 1348538Notes

Reaction equation

HRID 1348538 reaction equation
[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Na+].Br[CH2:8][CH2:9][CH2:10][O:11][Si:12]([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>O1CCCC1>[CH3:13][Si:12]([CH3:15])([CH3:14])[O:11][CH2:10][CH2:9][CH2:8][C:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 78681Sodium, 2,4-cyclopentadien-1-yl-HCID 5872321-Trimethylsiloxy-3-bromo-propane

Product 1

HCID 23303768(3-Trimethylsiloxypropyl)-cyclopentadieneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 50 ml of a 2.3 M solution of sodium cyclopentadienylide (115 mmol), a solution of 24.3 g (115 mmol) of 3-bromo-1-trimethylsiloxypropane in tetrahydrofurane is added. The quick formation of a pinkish solid is observed. The reaction is maintained under stirring for 12 hours and then it is neutralised with an ammonium chloride solution; the organic phase is extracted and concentrated to dryness in order to give an orange oil. (9.8 g, 50 mmol. Yield: 43%). 1H-NMR (CDCl3): 6.47–6.00 (m, 3H), 3.62 (m, 2H), 2.95 (m, 1H), 2.87 (m, 1H), 2.43 (m, 2H), 1.80 (m, 2H), 0.17 (s, 9H).

Workup

  1. temperatureThe reaction is maintained
  2. extractionthe organic phase is extracted
  3. concentrationconcentrated to dryness in order
  4. customto give an orange oil

Sources & evidence

ORD record
ord-a4528f76be924b91a658fcb1b32c97a0
Source dataset
uspto-grants-2007_05
Patent number
US07211538B2

Reaction notes

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