Chlorotrimethylsilane → HCID 15852795, compound

HRID 1354098Notes

Reaction equation

HRID 1354098 reaction equation
Br[C:2]1([CH2:9][CH2:10][CH3:11])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].Cl[Si:13]([CH3:16])([CH3:15])[CH3:14].CN(CCN(C)C)C>C1COCC1.[Zn]>[CH3:14][Si:13]([CH3:16])([CH3:15])[O:8][C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]=1[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 15441975HCID 15441975, compound

Product 1

HCID 15852795HCID 15852795, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-bromo-2-propylcyclohexanone (6.21 g, 28.3 mmol) and chlorotrimethylsilane (9.35 mL, 8.0 g, 73.7 mmol) in 65 mL THF was added dropwise to a slurry of Zn (2.78 g, 42.5 mmol) and TMEDA (2.2 mL, 1.65 g, 14.2 mmol) in 35 mL THF cooled in an ice bath. The mixture was allowed to stir in the cold for an additional 1.5 hrs, then allowed to warm to room temp. The mixture was filtered to remove the insolubles. The solvent was evaporated under reduced pressure and the residue extracted with Et2O (200 mL in 2 portions). The combined ethereal extracts were evaporated under reduced pressure and the residue fractionated under reduced pressure. A fraction boiling at 92°-96° (13 torr) was collected to afford 4.79 g (80%) of trimethyl(2-propylcyclohex-1-enyloxy)silane. MS (EI) 212 M(+).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe mixture was filtered
  3. customto remove the insolubles
  4. customThe solvent was evaporated under reduced pressure
  5. extractionthe residue extracted with Et2O (200 mL in 2 portions)
  6. customThe combined ethereal extracts were evaporated under reduced pressure
  7. customA fraction boiling at 92°-96° (13 torr) was collected

Sources & evidence

ORD record
ord-7a55a53e7aa841f8a2591df918d4e56b
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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