Formic Acid → HCID 20160910, compound

HRID 247458Notes

Reaction equation

HRID 247458 reaction equation
[CH2:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH:6]([CH2:8][NH:9][CH:10]([CH3:12])[CH3:11])[O:5][C:4]1=[O:13])[CH3:2].[CH:20](O)=O.C=O>C(O)C.O>[CH2:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH:6]([CH2:8][N:9]([CH3:20])[CH:10]([CH3:12])[CH3:11])[O:5][C:4]1=[O:13])[CH3:2]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 15598483HCID 15598483, compound

Product 1

HCID 20160910HCID 20160910, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution containing 1.3 g of 3-ethyldihydro-5-[[(1-methylethyl)amino]methyl]-3-phenyl-2(3H)-furanone, 1.3 g of 90% formic acid, and 1.1 g of 37% formaldehyde in 15 ml of ethanol was refluxed 2.5 hrs. The solution was cooled and then diluted with water and washed with diethyl ether. The aqueous layer was made basic with dilute sodium hydroxide and extracted with diethyl ether. The ether extract was washed with saturated sodium chloride solution, dried over anhydrous potassium carbonate, and concentrated in vacuo to an oil. The oil was dried at 40°/1 mm to yield 1.0 g of the title compound, having the following elemental analysis:

Workup

  1. temperaturewas refluxed 2.5 hrs
  2. temperatureThe solution was cooled
  3. washwashed with diethyl ether
  4. extractionextracted with diethyl ether
  5. extractionThe ether extract
  6. washwas washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous potassium carbonate
  8. concentrationconcentrated in vacuo to an oil
  9. customThe oil was dried at 40°/1 mm

Sources & evidence

ORD record
ord-49f661c4d2ed403f87e6e10c18752ff0
Source dataset
uspto-grants-1987_11
Patent number
US04707499

Reaction notes

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