Pyridine → HCID 19437039, compound

HRID 1735169Notes

Reaction equation

HRID 1735169 reaction equation
[C:1](Cl)([C:3]([O:5][CH3:6])=[O:4])=[O:2].[O:8]([CH2:15][C:16]1[O:21][CH2:20][CH2:19][CH2:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:8]([CH2:15][C:16]1[O:21][CH2:20][CH2:19][CH2:18][C:17]=1[C:1](=[O:2])[C:3]([O:5][CH3:6])=[O:4])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 19437041HCID 19437041, compound

Product 1

HCID 19437039HCID 19437039, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

35 g (0.29 mol) of methoxalyl chloride are added dropwise to 31 g (0.16 mol) of 6-phenoxymethyl-2,3dihydropyran (Example 7c), 39.5 g (0.5 mol) of pyridine and 2.5 g (0.02 mol) of p-dimethylaminopyridine in 200 ml of methylene chloride. During this procedure, the reaction mixture warms up to 30°-35 ° C. Stirring is carried out overnight and the reaction mixture is then poured onto water. The aqueous phase is separated off and the organic phase is extracted once again with water. The organic phase is then dried over MgSO4 and evaporated down. The residue is purified by column chromatography using hexane/ethyl acetate mixtures. 16 g of starting material and 8.5 g (0.031 mol=19%, pale yellow oil) of the title compound are obtained.

Workup

  1. customwarms up to 30°-35 ° C
  2. additionthe reaction mixture is then poured onto water
  3. customThe aqueous phase is separated off
  4. extractionthe organic phase is extracted once again with water
  5. dry with materialThe organic phase is then dried over MgSO4
  6. customevaporated down
  7. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-46afc8f222304baca425f072dd396350
Source dataset
uspto-grants-1996_07
Patent number
US05536734

Reaction notes

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