Chlorotrimethylsilane → HCID 54408610, compound

HRID 2083681Notes

Reaction equation

HRID 2083681 reaction equation
[C:1]([C:3]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:4]=[CH:5][I:6])#[CH:2].C([Mg]Br)C.[CH3:21][Si:22]([CH3:25])([CH3:24])Cl.[Cl-].[NH4+]>C1COCC1>[I:6][CH:5]=[CH:4][C:3]([C:1]#[C:2][Si:22]([CH3:25])([CH3:24])[CH3:21])([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 54200727HCID 54200727, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 54408610HCID 54408610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.3 g. of dl-3-ethynyl-1-iodo-3-trimethylsilyloxy-1-octene in 10 ml. of THF is treated at 0° C. under N2 with 3 ml. of 3M ethyl magnesium bromide and stirred at 25° C. for 1/2 hour. The mixture is then treated at 0° C. with 3.5 ml. of trimethylchlorosilane and stirred at 25° C. for an additional 21/2 hours. The whole mixture is added to aqueous ammonium chloride solution and extracted with ether. After washing with brine and drying over magnesium sulfate, the extract is evaporated. Distillation of the residue gives the title product, as an oil, 2.5 g. b.p. 79°-81° C. (0.025 mm).

Workup

  1. additionThe mixture is then treated at 0° C. with 3.5 ml
  2. extractionextracted with ether
  3. washAfter washing with brine
  4. dry with materialdrying over magnesium sulfate
  5. customthe extract is evaporated
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-3b186fc6840e49cbba589c49e36e636c
Source dataset
uspto-grants-1978_04
Patent number
US04086269

Reaction notes

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