Ammonium Acetate → HCID 53239416, compound

HRID 2371056Notes

Reaction equation

HRID 2371056 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[S:14][C:13]4[C:15](=O)[CH2:16][CH2:17][CH2:18][C:12]=4[C:11]=3[CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].[BH3-]C#[N:28].[Na+]>CO>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[S:14][C:13]4[CH:15]([NH2:28])[CH2:16][CH2:17][CH2:18][C:12]=4[C:11]=3[CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67261783HCID 67261783, compound

Product 1

HCID 53239416HCID 53239416, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-phenyl-2,3-dihydrodibenzo[b,d]thiophen-4(1H)-one (0.28 g, 1.0 mmol, 1 eq), ammonium acetate (0.77 g, 10 eq) in MeOH (20 mL) was added NaBH3CN (160 mg, 2.5 eq) in one portion. The reaction mixture was heated to 50° C. and stirred for 20 h, After that the solvent was removed, diluted with saturated NaHCO3 and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the title compound (64 mg, 23%).

Workup

  1. customAfter that the solvent was removed
  2. additiondiluted with saturated NaHCO3
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cb34afc7f3044eb398ea3b66bbb57020
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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