Ammonium formate → HCID 57753420, compound

HRID 552686Notes

Reaction equation

HRID 552686 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:19][S:16]([C:13]1[CH:14]=[CH:15][C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59853664HCID 59853664, compound

Product 1

HCID 57753420HCID 57753420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 0.07 mmol 2-(3,6-Dihydro-2H-pyran-4-yl)-5-methanesulfonyl-benzoic acid (CAS: 847547-05-1) in 0.5 ml methanol under argon was added 20 mg Pd/C, followed by 0.07 mmol ammonium formate. The reaction mixture was refluxed for 30 minutes, filtered and evaporated. Water was added and the solution was acidified with 2N HCl to pH 1. The aqueous phase was extracted with dichloromethane. The combined organic phases were dried over Na2SO4 and evaporated to yield the title compound as a colorless oil. MS (m/e): 283.2([M−H], 100%).

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. filtrationfiltered
  3. customevaporated
  4. additionWater was added
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-982004671b6f41fa845f0d68604c5b3c
Source dataset
uspto-grants-2011_05
Patent number
US07951836B2

Reaction notes

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