Formaldehyde → HCID 19600154, compound

HRID 611070Notes

Reaction equation

HRID 611070 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:12]=[CH:11][O:10][CH:9]=1)[CH:2]=[CH2:3].[CH2:13]=O>C(O)(=O)C>[CH2:1]([N:4]1[CH2:5][CH2:6][CH2:7][C:8]2[CH:12]=[CH:11][O:10][C:9]=2[CH2:13]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 19600258HCID 19600258, compound

Product 1

HCID 19600154HCID 19600154, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1.803 g (10.912 mmol) of N-allyl-3-(3-furyl)propylamine in 50 ml of acetic acid, 1.06 g (13.1 mmol) of 37% aqueous formaldehyde was added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide, and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Sources & evidence

ORD record
ord-6ba0edb31d5a4bf78a3c385548071f03
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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