Ammonium Chloride → [2-(3-Nitrophenyl)cyclohex-1-enyl]methanol

HRID 1842072Notes

Reaction equation

HRID 1842072 reaction equation
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[N+:12]([C:15]1[CH:16]=[C:17]([C:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH:27]=[O:28])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].[BH4-].[Na+].[Cl-].[NH4+]>CO.C1COCC1>[N+:12]([C:15]1[CH:16]=[C:17]([C:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH2:27][OH:28])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 578272822-(3-Nitrophenyl)cyclohex-1-enecarbaldehyde

Product 1

HCID 57827168[2-(3-Nitrophenyl)cyclohex-1-enyl]methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cerium chloride heptahydrate (1.22 g) was added to a mixed solution of 2-(3-nitrophenyl)cyclohex-1-enecarbaldehyde obtained in Preparation Example 4-(1) (630 mg) in methanol (60.0 mL) and THF (20.0 mL) in an ice bath. Sodium borohydride (130 mg) was added to the reaction solution at the same temperature, followed by stirring for 30 minutes. A saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by NH-silica gel column chromatography to obtain the title compound (610 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto obtain a crude product
  7. customThe resulting crude product was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-90023669ae884380bef78344d4ac899b
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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