HCID 54187371, compound → HCID 54108263, compound

HRID 1976297Notes

Reaction equation

HRID 1976297 reaction equation
[CH3:1][C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH3:13])=[CH:7][C:8]=2[CH3:12])[O:3]1.[H][H]>CO.[Pd]>[CH3:1][C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH3:13])=[CH:7][C:8]=2[CH3:12])[O:3]1

Participants

5

Reactant 2

HCID 54187371HCID 54187371, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54108263HCID 54108263, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl (2,5,7,8-tetramethyl-2H-chromen-2-yl)acetate (20.00 g) in methanol (MeOH) (300 ml) was hydrogenated in the presence of 10% palladium on carbon (50% wet, 4.0 g) in one atmosphere of hydrogen at room temperature for 16 hours. The catalyst was filtered off and MeOH was removed under reduced pressure to give a residue. The residue was purified by chromatography over silica gel (AcOEt-hexane 3:97 as eluent) to give ethyl (2,5,7,8-tetramethylchroman-2-yl)acetate as an oil (18.72 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customMeOH was removed under reduced pressure
  3. customto give a residue
  4. customThe residue was purified by chromatography over silica gel (AcOEt-hexane 3:97 as eluent)

Sources & evidence

ORD record
ord-f75c7000c7ea454d8e08d48846913281
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

Loading…