HCID 19426838, compound → HCID 67732574, compound

HRID 741693Notes

Reaction equation

HRID 741693 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15]([C:19]#[C:20][CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[CH:4][CH:3]=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15](/[CH:19]=[CH:20]\[CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 19426838HCID 19426838, compound

Product 1

HCID 67732574HCID 67732574, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product of Step 2, above (14, 2.0 g, 6.8 mmol) and 5% Pd/BaSO4 (200 mg) in methanol was subjected to hydrogenation at atmospheric pressure. After the absorption of the required amount of hydrogen, the suspension was filtered and washed with methanol. Methanol was evaporated from the filtrate. The residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:4) to give 1.8 g (95% yield) of the title compound as pale yellow solids.

Workup

  1. customAfter the absorption of the required amount of hydrogen
  2. filtrationthe suspension was filtered
  3. washwashed with methanol
  4. customMethanol was evaporated from the filtrate
  5. customThe residue was purified by column chromatography on silica gel (eluent=ethyl acetate:n-hexane, 1:4)

Sources & evidence

ORD record
ord-9166079598d04ab9b1e15ae6126c2ad7
Source dataset
uspto-grants-1996_09
Patent number
US05552424

Reaction notes

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