Acetonitrile → HCID 178442135, compound

HRID 1849927Notes

Reaction equation

HRID 1849927 reaction equation
ClCCl.C([SiH]([CH2:9][CH3:10])CC)C.C(=O)([O-])O.[Na+].[C:16](#N)[CH3:17]>>[CH2:17]([C@H:16]1[CH2:10][CH2:10][C@H:9]([CH:17]2[CH2:16][CH:17]([CH2:9][CH2:16][CH2:17][CH2:9][CH3:10])[CH:16]=[CH:10][CH2:9]2)[CH2:17][CH2:16]1)[CH2:9][CH3:10]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 516892Sodium Bicarbonate

Product 1

HCID 178442135HCID 178442135, compound

Procedure

Under a nitrogen atmosphere, 6.56 g of compound (r-12) was dissolved into a mixed solvent of 100 mL of dichloromethane and 100 mL of acetonitrile, 3.91 g of triethylsilane was added thereto, and then 4.13 g of trifluoroborane-diethyl ether complex was added dropwise at −50° C., the resultant mixture was stirred at −78° C. for 30 minutes, and then stirred at room temperature for 1 hour. A saturated aqueous solution of sodium hydrogencarbonate was added dropwise to terminate a reaction, the resultant mixture was subjected to extraction with dichloromethane, and then organic layers were combined, the resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and then dried over anhydrous magnesium sulfate. A solvent was evaporated under reduced pressure, and the resultant residue was purified by fractionation on silica gel column chromatography (eluate:heptane), and further purified by recrystallization from ethyl acetate, and dried, and thus 1.11 g of 3-(4-(trans-4-propylcyclohexyl)-6-pentylcyclohexene (compound (1-1-1-3)) was obtained.

Workup

  1. additionwas added
  2. addition4.13 g of trifluoroborane-diethyl ether complex was added dropwise at −50° C.
  3. customto terminate
  4. customa reaction
  5. extractionthe resultant mixture was subjected to extraction with dichloromethane
  6. washthe resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customA solvent was evaporated under reduced pressure
  9. customthe resultant residue was purified by fractionation on silica gel column chromatography (eluate:heptane)
  10. customfurther purified by recrystallization from ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-062ffa3fe3a046cbab5b0a5dbd518f63
Source dataset
uspto-grants-2015_02
Patent number
US08956552B2

Reaction notes

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