Triethylamine → HCID 67609631, compound

HRID 78747Notes

Reaction equation

HRID 78747 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1(Br)[CH2:11][CH2:10][O:9][CH:8]1[O:12][CH3:13])=[O:6])[CH3:2].C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH:7]1[CH2:11][CH2:10][O:9][CH:8]1[O:12][CH3:13])=[O:6])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67607880HCID 67607880, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67609631HCID 67609631, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl-2-(3-bromo-2-methoxytetrahydrofuran-3-yl)-2-oxoacetate (8.5 g) was dissolved in Ethanol (85 ml). Triethyl amine (3.66 g) was added to the reaction mass. 5% Palladium on Carbon (0.85 g) was added and reaction was hydrogenated at 4-5 kg pressure of Hydrogen for 8 hrs. Reaction mass was filtered through hyflow and concentrated to residue. This residue was slurried in methyltert-butylether (42 ml) and filtered to remove triethylamine HBr salt. Filtrate was concentrated to get oily residue of Ethyl-2-(2-methoxytetrahydrofuran-3-yl)-2-oxoacetate (yield 6.0 g).

Workup

  1. customreaction
  2. customReaction mass
  3. filtrationwas filtered through hyflow
  4. concentrationconcentrated to residue
  5. filtrationfiltered
  6. customto remove triethylamine HBr salt
  7. concentrationFiltrate was concentrated

Sources & evidence

ORD record
ord-ebbc25a263864c7ebfdd52970f939874
Source dataset
uspto-grants-2014_09
Patent number
US08841467B2

Reaction notes

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