Tetrabutylammonium Fluoride → Methyl 6-amino-2-hydroxy-3-[2-(2-hydroxyethyl)-furan-3-yl]-benzoate

HRID 1778352Notes

Reaction equation

HRID 1778352 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[NH2:19][C:20]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([OH:30])[C:23]([C:31]2[CH:35]=[CH:34][O:33][C:32]=2[CH2:36][CH2:37][O:38][Si](C(C)(C)C)(C)C)=[CH:22][CH:21]=1>C1COCC1>[NH2:19][C:20]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([OH:30])[C:23]([C:31]2[CH:35]=[CH:34][O:33][C:32]=2[CH2:36][CH2:37][OH:38])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86684732Methyl 6-amino-3-{2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl}-2-hydroxybenzoate2×

Product 1

HCID 66685676Methyl 6-amino-2-hydroxy-3-[2-(2-hydroxyethyl)-furan-3-yl]-benzoateYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1M solution in THF, 25 mL) was added to a solution of methyl 6-amino-3-{2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl}-2-hydroxybenzoate (Intermediate 29, 1.34 g) in THF (75 mL) and the mixture was stirred for 1 hour. The mixture was evaporated to dryness and water and ethyl acetate were added. The organic layer was separated, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-50% to give methyl 6-amino-2-hydroxy-3-[2-(2-hydroxyethyl)-furan-3-yl]-benzoate (0.88 g) as a yellow gum.

Workup

  1. customThe mixture was evaporated to dryness and water and ethyl acetate
  2. additionwere added
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-50%

Sources & evidence

ORD record
ord-5d4d5f8449b948c1a2076fe5792c3140
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

Loading…