HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Formaldehyde → HCID 11776435, compound

HRID 1720672
Notes
Print preview

Reaction equation

HRID 1720672 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 270093Ethyl 2-(diethoxyphosphoryl)-3-(naphthalen-1-yl)propanoateHCID 433294Lithium Chloride

Product 1

HCID 11776435HCID 11776435, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Procedure

1.92 g of lithium chloride was suspended-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-598ffbb2a52d42c881e6a0ee975d2a3b
Source dataset
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05506356

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes