Pentane → HCID 54342566, compound

HRID 1199545Notes

Reaction equation

HRID 1199545 reaction equation
[Br:1][CH:2]=[CH:3][CH:4]=[C:5]([CH3:9])[CH2:6][CH:7]=[O:8].CCCCC.C(N(CC)CC)C.Br[Si:23]([CH3:26])([CH3:25])[CH3:24]>C(#N)C>[Br:1][CH:2]=[CH:3][CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][O:8][Si:23]([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 8003PentaneHCID 8471TriethylamineHCID 76113BromotrimethylsilaneHCID 544165006-Bromo-3-methylhexa-3,5-dienal

Product 1

HCID 54342566HCID 54342566, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

6-Bromo-3-methyl-3,5-hexadienal (0.95 g; 5 mmol) dissolved in acetonitrile (25 cc) and pentane (25 cc) is introduced, under an argon atmosphere, into a 100-cc round flask fitted with a septum and a magnetic stirrer. Triethylamine (1 g; 10 mmol, i.e. 2 equivalents) is then added. After the mixture has been cooled to 0° C., bromotrimethylsilane (1.53 g; 2 equivalents) is added dropwise. The temperature is allowed to return to about 20° C. After 48 hours the reaction is complete. The acetonitrile phase is extracted with pentane (4×15 cc) under an argon atmosphere. After evaporation of the solvent and distillation, 6-bromo-3-methyl-1-trimethylsilyloxy-1,3,5-hexatriene (0.53 g) is obtained (b.p. 0.06 kPa=92°-95° C.). The yield is 46.8%. The structure of the product obtained is confirmed by the infrared spectrum and the proton nuclear magnetic resonance spectrum.

Workup

  1. customfitted with a septum and a magnetic stirrer
  2. customto return to about 20° C
  3. extractionThe acetonitrile phase is extracted with pentane (4×15 cc) under an argon atmosphere
  4. customAfter evaporation of the solvent and distillation

Sources & evidence

ORD record
ord-7735f9d42bb04e05b4be3d58efc3efb5
Source dataset
uspto-grants-1990_02
Patent number
US04900858

Reaction notes

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