Ammonium Chloride → HCID 178442327, compound

HRID 1849923Notes

Reaction equation

HRID 1849923 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH:19]=[CH:18]3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[Cl-].[NH4+]>C1COCC1>[CH2:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][C:20]([CH2:3][CH2:2][CH2:1][CH2:5][CH3:6])([OH:23])[CH:19]=[CH:18]3)[CH2:13][CH2:12]2)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 178445602HCID 178445602, compound

Product 1

HCID 178442327HCID 178442327, compoundYield 145.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 3.0 g of 4-(4-(trans-4-butylcyclohexyl)cyclohexyl)-2-cyclohexenone (r-3) was dissolved into 50 mL of THF, 11.4 mL of pentylmagnesium bromide THF solution (1 M/L) was added dropwise thereto, and the resultant mixture was stirred at 50° C. for 30 minutes, and then stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride was added dropwise under ice-cooling, the resultant mixture was subjected to extraction with ethyl acetate, and then organic layers were combined, the resultant organic layer was washed with 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:ethyl acetate=7:3 (in a volume ratio)), and thus 2.68 g of 4-(4-(trans-4-butylcyclohexyl)cyclohexyl)-1-pentyl-2-cyclohexene-1-ol (compound (r-4)) was obtained.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. extractionthe resultant mixture was subjected to extraction with ethyl acetate
  4. washthe resultant organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customA solvent was evaporated under reduced pressure
  7. customthe resultant residue was purified by fractionation on silica gel column chromatography (eluate:heptane

Sources & evidence

ORD record
ord-dc27201fc68547cfbf4dd8b9fbc3fc56
Source dataset
uspto-grants-2015_02
Patent number
US08956552B2

Reaction notes

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