Ammonium Chloride → HCID 67058220, compound

HRID 1515112Notes

Reaction equation

HRID 1515112 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12].[BH4-].[Na+].[Cl-].[NH4+]>CO.O1CCCC1>[CH2:6]1[CH:7]([OH:12])[C:8]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:14])[F:13])[C:4]=2[CH2:5]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 219210934-(Trifluoromethyl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 67058220HCID 67058220, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(Trifluoromethyl)indan-1-one (300 mg, 1.50 mmol) was dissolved in methanol (2.5 mL) and tetrahydrofuran (2.5 mL), and sodium borohydride (85 mg, 2.25 mmol) was added thereto at 0° C., and then, the resulting mixture was stirred at room temperature for 2 hours. To the reaction solution, a saturated aqueous solution of ammonium chloride was added, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 67:33 (v/v)), whereby the objective title compound was obtained as a white solid (291 mg, yield: 96%).

Workup

  1. extractionthe organic matter was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  6. customwas obtained
  7. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 67:33 (v/v)), whereby the objective title compound

Sources & evidence

ORD record
ord-10f84a76bafa488e82d0bb751099ed65
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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