HCID 20239567, compound → HCID 20239563, compound

HRID 364652Notes

Reaction equation

HRID 364652 reaction equation
[CH3:1][C:2]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:3]=1[C:4]([C:20]#[CH:21])([OH:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:7][CH:6]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:3]=1[C:4]([CH2:20][CH3:21])([OH:19])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][N:14]([CH2:15][CH3:16])[CH2:17][CH3:18])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 20239567HCID 20239567, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20239563HCID 20239563, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10.5 g. of 2,5-dimethyl-4'-[2-(diethylamino)-ethoxy]-α-ethinyl-benzhydrol are dissolved in 110 ml. of methanol, and 0.5 g. of a 10% palladium-on-charcoal catalyst are added to the mixture. The reaction mixture is hydrogenated until the uptake of the calculated amount of hydrogen is complete. Thereafter the catalyst is filtered off, and the solvent is evaporated in vacuo. Recrystallization of the solid residue obtained from a mixture of n-hexane and ethyl acetate yields 9.1 g. of the title compound, melting at 89° to 90° C.

Workup

  1. filtrationThereafter the catalyst is filtered off
  2. customthe solvent is evaporated in vacuo
  3. customRecrystallization of the solid residue
  4. customobtained from a mixture of n-hexane and ethyl acetate
  5. customyields 9.1 g

Sources & evidence

ORD record
ord-eaa40b0bc702490abdad29f8a457df3e
Source dataset
uspto-grants-1986_08
Patent number
US04605672

Reaction notes

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