HCID 20164613, compound → HCID 20164683, compound

HRID 255842Notes

Reaction equation

HRID 255842 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][C:5]([C:13]([O:15][CH3:16])=[CH2:14])([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:6]>[Pd].C(O)(=O)C>[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][C:5]([CH:13]([O:15][CH3:16])[CH3:14])([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:6]

Participants

4

Reactant 1

HCID 20164613HCID 20164613, compound

Product 1

HCID 20164683HCID 20164683, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2.0 g of α-(2,4-dichlorobenzyl)-α-(1-methoxyvinyl)-3-pyridinemethanol (see Example 3, 2nd end product), 0.2 g of hydrogenation catalyst (5% palladium on carbon) and 40 ml of acetic acid is stirred for 7 hours at room temprature under a hydrogen atmosphere at normal pressure. Thereafter, the hydrogenation catalyst is removed by filtration, the filtrate is freed from solvent under reduced pressure, the residue is taken up in a saturated sodium bicarbonate solution and the solution is extracted with ethyl acetate. The organic phase is evaporated and the residue is crystallized from methylene chloride/n-hexane. In this manner there is obtained α-(2,4-dichlorobenzyl)-α-(1-methoxyethyl)-3-pyridinemethanol as colorless crystals, m.p. 94°-95° C.

Workup

  1. customThereafter, the hydrogenation catalyst is removed by filtration
  2. extractionthe solution is extracted with ethyl acetate
  3. customThe organic phase is evaporated
  4. customthe residue is crystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-75e223deaaa9454d85e5c6315ba7c4c9
Source dataset
uspto-grants-1987_10
Patent number
US04699652

Reaction notes

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