Formaldehyde → HCID 22065274, compound

HRID 1026184Notes

Reaction equation

HRID 1026184 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=[O:23])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1.C=O.Cl.[CH3:27]NC.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=[O:23])[C:12]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)=[CH2:27]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 10473Dimethylamine, hydrochlorideHCID 873120HCID 873120, compound

Product 1

HCID 22065274HCID 22065274, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Compound V (10.0 g, 31.6 mmol), paraformaldehyde (6.4 g), dimethylamine hydrochloride (9.4 g, 115 mmol) and sodium carbonate (13.3 g, 125 mmol) was dissolved in tetrahydrofuran (150 mL) and heated under reflux for 16 h. The reaction was cooled to room temperature, filtered and the filtrate was concentrated under reduced pressure to give a brown oil. Purification by column chromatography on silica gel 60, eluting with hexane/ethyl acetate (2:1 to 1:1) afforded Compound IV (5.3 g, 16 mmol, 51%) as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give a brown oil
  6. customPurification by column chromatography on silica gel 60
  7. washeluting with hexane/ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-98eb12c6508a487a909fe64095bfbc78
Source dataset
uspto-grants-2014_05
Patent number
US08729134B2

Reaction notes

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