Tetrahydrofuran → HCID 178440475, compound

HRID 1849928Notes

Reaction equation

HRID 1849928 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+].[CH2:27]1[CH2:31]OC[CH2:28]1>>[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]([CH2:28][CH2:27][CH3:31])([OH:24])[CH:20]=[CH:19]2)[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178466565HCID 178466565, compound

Product 1

HCID 178440475HCID 178440475, compound

Procedure

Under a nitrogen atmosphere, 4.97 g of 4-(trans-4-(2,3-difluoro-4-ethyloxyphenyl)cyclohexyl)-2-cyclohex enone (r-15) was dissolved into 60 mL of THF, 18.0 mL of propylmagnesium 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 3.79 g of 4-(trans-4-(2,3-difluoro-4-ethyloxyphenyl)cyclohexyl)-1-propyl-2-cyclohexene-1-ol (compound (r-16)) 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-fe8e3a4998824676b06bf923282330bc
Source dataset
uspto-grants-2015_02
Patent number
US08956552B2

Reaction notes

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