Chlorotriethylsilane → HCID 86710069, compound

HRID 1468277Notes

Reaction equation

HRID 1468277 reaction equation
[F:1][C:2]1([F:19])[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([C:12]2([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]2)=[O:11])[CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1.Cl[Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34]>C1COCC1>[F:1][C:2]1([F:19])[CH2:3][CH2:4][CH:5]([CH2:8][CH:9]=[C:10]([C:12]2([C:15]([F:16])([F:17])[F:18])[CH2:13][CH2:14]2)[O:11][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 13819ChlorotriethylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86710067HCID 86710067, compound

Product 1

HCID 86710069HCID 86710069, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4,4-Difluorocyclohexyl)-1-(1-trifluoromethylcyclopropyl)propan-1-one (0.200 g, 0.704 mmol) obtained in step 3 was dissolved in THF (2.0 mL). Under ice-cooled condition, DBU (0.117 mL, 0.774 mmol) and chlorotriethylsilane (0.130 mL, 0.774 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with heptane after adding a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→90/10) to give {3-(4,4-difluorocyclohexyl)-1-(1-trifluoromethylcyclopropyl)prop-1-enyloxy}triethylsilane (0.253 g, yield 90%).

Workup

  1. additionwere added
  2. extractionThe reaction mixture was extracted with heptane
  3. additionafter adding a saturated sodium hydrogen carbonate aqueous solution
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→90/10)

Sources & evidence

ORD record
ord-192503a9c4aa410fbfb116c92f89015f
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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