Ammonium Chloride → HCID 178442328, compound

HRID 1530180Notes

Reaction equation

HRID 1530180 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C@H:12]1[CH2:17][CH2:16][C@H:15]([CH:18]2[CH2:23][CH2:22][C:21](=[O:24])[CH:20]=[CH:19]2)[CH2:14][CH2:13]1.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C@H:12]1[CH2:13][CH2:14][C@H:15]([CH:18]2[CH2:23][CH2:22][C:21]([CH2:4][CH2:3][CH2:2][CH2:7][CH3:6])([OH:24])[CH:20]=[CH:19]2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 178466565HCID 178466565, compound

Product 1

HCID 178442328HCID 178442328, compoundYield 141.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 4.00 g of 4-(trans-4-(2,3-difluoro-4-ethyloxyphenyl)cyclohexyl)-2-cyclohex enone (r-15) was dissolved into 60 mL of THF, 14.4 mL of pentylmagnesium bromide THF solution (1 M/L) was added dropwise thereto at room temperature, 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=6:4), and thus 3.45 g of 4-(trans-4-(2,3-difluoro-4-ethyloxyphenyl)cyclohexyl)-1-pentyl-2-cyclohexene-1-ol (compound (r-17)) 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:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-642ce67b45a0487ab8b9e445c8b13f0b
Source dataset
uspto-grants-2015_07
Patent number
US09090825B2

Reaction notes

Loading…