Ammonium Chloride → HCID 178442327, compound

HRID 1530175Notes

Reaction equation

HRID 1530175 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-1ddc7f81db90408ca3a5b437d7566fe4
Source dataset
uspto-grants-2015_07
Patent number
US09090825B2

Reaction notes

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