Hydrochloric Acid → Dimethyl(1-octenyl)(2-pyridyl)silane

HRID 1266558

Reaction equation

HRID 1266558 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH3:28][SiH:29]([CH3:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1.Cl>C(OCC)C>[CH3:28][Si:29]([CH3:36])([CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 123701-OctyneHCID 91999694HCID 91999694, compound

Product 1

HCID 53632469Dimethyl(1-octenyl)(2-pyridyl)silaneYield 90.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
40 °C

Procedure

To 1.0 ml of diethyl ether were added 10 mg (0.25 μmol) of bis(cyclooctadiene)platinum, 13 mg (0.50 μmol) of triphenylphosphine and 165 mg (1.5 mmol) of 1-octyne, and 69 mg (0.5 mmol) of dimethyl(2-pyridyl)silane was added dropwise thereto at room temperature over 1 hour. Further, the mixture was continued to be stirred for 6 hours at an inner temperature of 40° C., followed by the addition of 6 ml of 1N hydrochloric acid and 5 ml of diethyl ether. After the mixture was stirred for 30 minutes, it was left stand and separated into the organic and aqueous layers. The organic layer was extracted with five portions of 6 ml of 1N hydrochloric acid, and the resulting aqueous layers were combined together and turned basic with the addition of sodium hydroxide pellets. This aqueous layer was extracted with three portions of 10 ml of diethyl ether. The resulting organic layer was dried over magnesium sulfate and the solvent was evaporated off under reduced pressure to give 112 mg of dimethyl(1-octenyl)(2-pyridyl)silane. Yield: 90%.

Workup

  1. additionwas added dropwise
  2. stirringAfter the mixture was stirred for 30 minutes
  3. waitit was left stand
  4. customseparated into the organic and aqueous layers
  5. extractionThe organic layer was extracted with five portions of 6 ml of 1N hydrochloric acid
  6. additionturned basic with the addition of sodium hydroxide pellets
  7. extractionThis aqueous layer was extracted with three portions of 10 ml of diethyl ether
  8. dry with materialThe resulting organic layer was dried over magnesium sulfate
  9. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-ec285a85be014e9ebe6187b6299f4e8d
Source dataset
uspto-grants-2003_04
Patent number
US06548673B1

Linked notes

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