Formaldehyde → HCID 22418871, compound

HRID 2255740Notes

Reaction equation

HRID 2255740 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)[N:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:28]1CCN2C(=NCCC2)CC1.C1COCC1.C=O>C1COCC1>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([CH2:17][C:11](=[CH2:28])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 433294Lithium ChlorideHCID 53873427HCID 53873427, compoundHCID 86745927HCID 86745927, compound

Product 1

HCID 22418871HCID 22418871, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

140 mg of anhydrous lithium chloride was dissolved in 7 ml of dry THF, and 3 ml of a THF solution of 1.04 g of ethyl 2-diethylphosphono-3-(4-quinolyl)propionate was added thereto. Then, 1.7 ml of DBU/THF (12/25) was added, and then a 3 ml of a THF solution of 0.14 g of paraformaldehyde was added thereto. The mixture was stirred at room temperature for one hour, and then the insoluble materials were removed by filtration. The product collected by filtration was washed with a small amount of benzene, and the washed solution was combined with the filtrate. The combined filtrate was diluted with 60 ml of ethyl acetate and washed with 40 ml of water and then with 40 ml of a saturated sodium chloride aqueous solution. The organic layer was separated, dried over anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to obtain 601 mg of the above identified compound as syrup.

Workup

  1. customthe insoluble materials were removed by filtration
  2. filtrationThe product collected by filtration
  3. washwas washed with a small amount of benzene
  4. additionThe combined filtrate was diluted with 60 ml of ethyl acetate
  5. washwashed with 40 ml of water
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)
  10. customto obtain 601 mg of the

Sources & evidence

ORD record
ord-9fb07099b4b84290a7b5de209235a878
Source dataset
uspto-grants-1993_08
Patent number
US05240924

Reaction notes

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