Chlorotrimethylsilane → HCID 20541498, compound

HRID 1065139Notes

Reaction equation

HRID 1065139 reaction equation
C[Si](C)(C)[O:3][CH:4]([CH:7]=[CH2:8])[CH:5]=[CH2:6].C([Li])(CC)C.[CH3:16][C:17]1[C:18](=[O:25])[C:19]([CH3:24])([CH3:23])[CH:20]=[CH:21][CH:22]=1.[CH3:26][Si:27](Cl)([CH3:29])[CH3:28].[F-].[K+].[NH4+].[Cl-]>O1CCCC1.C1CCCCC1.CN(C)P(=O)(N(C)C)N(C)C.CO>[O:3]=[C:4]([CH:5]=[CH2:6])[CH2:7][CH2:8][C:18]1([O:25][Si:27]([CH3:29])([CH3:28])[CH3:26])[C:19]([CH3:24])([CH3:23])[CH:20]=[CH:21][CH:22]=[C:17]1[CH3:16]

Participants

11

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 835282,6,6-Trimethylcyclohexa-2,4-dienoneHCID 522689Potassium FluorideHCID 12749247HCID 12749247, compoundHCID 178418400CID 53628100

Product 1

HCID 20541498HCID 20541498, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of 400 mg 3-trimethylsilyloxy-1,4-pentadiene in 3 ml of tetrahydrofuran at -78° under argon was added a solution of 2.3 ml of sec-butyllithium in cyclohexane and the solution stirred for 15 minutes. Then, a solution of 275 mg. of 2,6,6-trimethylcyclohexa-2,4-dienone in 1 ml of tetrahydrofuran was added. After 5 minutes, 332 mg of trimethylsilyl chloride in 2 ml of hexamethylphosphoric acid triamide was added and the mixture left for 1 hour at -78°. After working up as in Example 1(a) the crude product mixture was diluted with 20 ml of methanol cooled to 0° and 224 mg of potassium fluoride were added. After 1 hour at 0°-5°, the mixture was poured into saturated aqueous NH4Cl solution and extracted with ether. Chromatography (SiO2, toluene) of the evaporated extract gave 329 mg of 1-[3-oxo-pent-4 -en-1-yl]-1-trimethylsilyloxy-2,6,6-trimethylcyclohexa-2,4-diene (56% yield) characteristics as above.

Workup

  1. waitAfter 5 minutes
  2. waitthe mixture left for 1 hour at -78°
  3. temperaturecooled to 0°
  4. waitAfter 1 hour at 0°-5°
  5. extractionextracted with ether
  6. extractionChromatography (SiO2, toluene) of the evaporated extract

Sources & evidence

ORD record
ord-86396ca99fec4357bf0fe636247c1156
Source dataset
uspto-grants-1982_05
Patent number
US04328352

Reaction notes

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