Acetonitrile → 1-Bromo-2-methyl-4-trimethylsilyloxybutadiene

HRID 2352383Notes

Reaction equation

HRID 2352383 reaction equation
C(#N)C.[Br:4][CH2:5][C:6]([CH3:10])=[CH:7][CH:8]=[O:9].Br[Si:12]([CH3:15])([CH3:14])[CH3:13]>CCCCC.C(N(CC)CC)C>[Br:4][CH:5]=[C:6]([CH3:10])[CH:7]=[CH:8][O:9][Si:12]([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 76113BromotrimethylsilaneHCID 541144354-Bromo-3-methyl-2-butenal

Product 1

HCID 540133491-Bromo-2-methyl-4-trimethylsilyloxybutadieneYield 25.8%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolvent4×HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

Pentane (120 cc), acetonitrile (120 cc), 4-bromo-3-methyl-2-butenal (9 g, 107 mmol) and triethylamine (13 g) are introduced under an argon atmosphere into a 500-cc three-necked round-bottomed flask. The temperature is kept at 0° C. and bromotrimethylsilane (19.6 g) is then added over 20 minutes. The mixture is stirred for 2 days at a temperature in the region of 20° C. The pentane solution is sampled with a syringe and is then replaced with an equivalent quantity of pentane. The operation is repeated 4 times. The various pentane solutions are combined and the pentane is removed, any entry of air being excluded. The residue obtained is purified by distillation. 1-Bromo-2-methyl-4-trimethylsilyloxybutadiene (6.5 g) is thus obtained (B.P.0.25 =59° C.).

Workup

  1. customis kept at 0° C.
  2. customthe pentane is removed
  3. customThe residue obtained
  4. distillationis purified by distillation

Sources & evidence

ORD record
ord-c8711508eddb401492ac4485b686e484
Source dataset
uspto-grants-1989_10
Patent number
US04876370

Reaction notes

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