Formaldehyde → HCID 57485792, compound

HRID 749138Notes

Reaction equation

HRID 749138 reaction equation
[CH:1]1([CH2:7][NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C=O.[C:16](=O)([O-])[O-:17].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[OH:17][CH2:16][N:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)[C:9](=[O:13])[O:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 57485791HCID 57485791, compound

Product 1

HCID 57485792HCID 57485792, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sample of ethyl cyclohex-3-en-1-ylmethylcarbamate (5.1 g, 28 mmol) in 500 mL of THF was treated with paraformaldehyde (16.7 g, 560 mmol), potassium carbonate (7.8 g, 56 mmol) and cesium carbonate (1.8 g, 5.6 mmol). The mixture was stirred vigorously and heated under reflux for 4 h. The mixture was cooled, filtered and concentrated under reduced pressure. The residue was column chromatographed on silica gel, using 3:1 hexane/ethyl acetate as eluent, to give a colorless oil (3.6 g, 61%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-30aafcb6d931489da6d82360d1e0b301
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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