Formaldehyde → HCID 14424159, compound

HRID 2231384Notes

Reaction equation

HRID 2231384 reaction equation
C([C:3]1([O:12]C(=O)C)[CH2:8][C:7]2([CH3:10])[O:9][C:4]1([CH3:11])[CH:5]=[CH:6]2)#N.C[O-].[Na+].C=O>CO>[CH3:11][C:4]12[O:9][C:7]([CH3:10])([CH:6]=[CH:5]1)[CH2:8][C:3]2=[O:12]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10942334Sodium MethoxideHCID 14424156HCID 14424156, compound

Product 1

HCID 14424159HCID 14424159, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 12 g of 2-cyano-2-acetoxy-1,4-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene in 100 ml of methanol was added 0.028 mole of sodium methoxide. The mixture was stirred at room temperature for 3 hours, then 30 ml of formalin was added and the mixture was stirred an additional hour at room temperature. The reaction mixture was washed with 100 ml of water, then with 100 ml of saturated sodium chloride solution and extracted thrice with 100 ml of methylene chloride, dried (Na2SO4), concentrated and flash chromatographed using 1:1 hexane:methylene chloride as eluent to give 6 g of the desired product as a yellow oil.

Workup

  1. stirringthe mixture was stirred an additional hour at room temperature
  2. washThe reaction mixture was washed with 100 ml of water
  3. extractionwith 100 ml of saturated sodium chloride solution and extracted thrice with 100 ml of methylene chloride
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customflash chromatographed

Sources & evidence

ORD record
ord-50cf2d7ed3e64988a0ceabddedc10096
Source dataset
uspto-grants-1988_11
Patent number
US04782169

Reaction notes

Loading…