Ethyl Acetate → HCID 66969636, compound

HRID 1360170Notes

Reaction equation

HRID 1360170 reaction equation
O[N:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([OH:9])[CH:3]1O.[C:11](OC([O-])=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(OC(=O)C)C>O1CCCC1.O>[OH:9][C:4]1[CH2:3][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7]([OH:8])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 22064466Tert-butyldicarbonateHCID 66969881HCID 66969881, compound

Product 1

HCID 66969636HCID 66969636, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

1 g (12 mmol) of 1,2,3,6-tetrahydroxypyridine and 2.76 g (12.6 mmol) of t-butyl dicarbonate was dissolved in 40 mL of tetrahydrofurane/water (1:1), and after stirring for 5 hour, 100 mL of ethylacetate was added thereto. After washing with water, an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 2.1 g (11.5 mmol) of the title compound in a yield of 91%.

Workup

  1. washAfter washing with water
  2. dry with materialan organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ece30b44fd3749019622f6c965b8d9c5
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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