Formaldehyde → HCID 11776435, compound

HRID 1109410Notes

Reaction equation

HRID 1109410 reaction equation
[Cl-].[Li+].C(OP([CH:11]([CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:28]1CCN2C(=NCCC2)CC1.C=O>C1COCC1>[C:18]1([CH2:17][C:11](=[CH2:28])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 270093NSC112269HCID 433294Lithium Chloride

Product 1

HCID 11776435HCID 11776435, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1.92 g of lithium chloride was sun-pended in 50 ml of dry THF, and 15 g of ethyl 2-diethylphosphono-3-(1-naphthyl)propionate was dropwise added thereto. Then, 16 ml of a 50% dry THF solution of DBU was dropwise added thereto, and 2.01 g of paraformaldehyde suspended in dry THF was added thereto. The mixture was stirred at room temperature for 3 hours, and the insolubles were removed by filtration and washed with a small amount of diethyl ether. The washing solution and and the filtrate were put together, and the solvent was distilled off. The resulting syrup was dissolved in 180+ml of diethyl ether. The diethyl ether layer was washed sequentially with a 10% citric acid aqueous solution, with water and with a saturated sodium chloride aqueous solution and dried over anhydride sodium sulfate. The solvent was distilled off, and the syrup thereby obtained was purified by silica gel column chromatography (n-hexane/diethyl ether=20/1) to obtain 6.48 g of ethyl 2-(1-naphthyl)methyl-2-propenoate as colorless oily substance.

Workup

  1. additionwas added
  2. customthe insolubles were removed by filtration
  3. washwashed with a small amount of diethyl ether
  4. distillationthe solvent was distilled off
  5. dissolutionThe resulting syrup was dissolved in 180+ml of diethyl ether
  6. washThe diethyl ether layer was washed sequentially with a 10% citric acid aqueous solution, with water and with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydride sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe syrup thereby obtained
  10. customwas purified by silica gel column chromatography (n-hexane/diethyl ether=20/1)

Sources & evidence

ORD record
ord-70cb32d7b55f4a86bb4ecd61e9bb325e
Source dataset
uspto-grants-1994_06
Patent number
US05319082

Reaction notes

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