Ammonium Chloride → HCID 66781618, compound

HRID 1095256Notes

Reaction equation

HRID 1095256 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([F:10])=[C:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][CH2:12]2)[CH:7]=[CH:6][C:5]=1[CH:22]1[CH2:27][CH2:26][CH:25]([CH:28]2[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]2)[CH2:24][CH2:23]1.[H][H].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:3][C:4]1[C:9]([F:10])=[C:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][CH2:12]2)[CH:7]=[CH:6][C:5]=1[CH:22]1[CH2:27][CH2:26][CH:25]([CH:28]2[CH2:29][CH2:30][CH:31]([OH:34])[CH2:32][CH2:33]2)[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 66781559HCID 66781559, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66781618HCID 66781618, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (1.37 g) and THF (60 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to 0° C. The compound (47) (15.3 g) dissolved in a THF (60 ml) was added dropwise thereto, with caution in the evolution of hydrogen gas, and the mixture was stirred for 3 hours. A saturated aqueous solution of ammonium chloride (300 ml) and ethyl acetate (300 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed with brine, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=5:1 by volume) as an eluent and silica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane:Solmix=1:1 by volume), and dried, giving 12.0 g of 4′-(2,3-difluoro-4-(4-pentylcyclohexyl)phenyl)bi(cyclohexane)-4-ol (48). The yield based on the compound (47) was 78.3%.

Workup

  1. additionwas added dropwise
  2. additionmixed
  3. customhad separated into organic and aqueous phases
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe residue was purified with a fractional operation by means of column chromatography
  8. customsilica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane:Solmix=1:1 by volume)
  9. customdried

Sources & evidence

ORD record
ord-24e14f9c4e8848ffbba51eb95e4c7718
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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