Fluoride Ion → ethyl (4-hydroxy-1H-indol-1-yl)acetate

HRID 2389368Notes

Reaction equation

HRID 2389368 reaction equation
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(C(C)(C)C)(C)C.[F-]>C1COCC1>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 68822793ethyl (4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-1-yl)acetate

Product 1

HCID 68822476ethyl (4-hydroxy-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-1-yl)acetate (3.7 g) in THF (74 mL) was added tetra n-butylammomium fluoride (3.5 g) at ambient temperature. The reaction mixture was stirred at the same temperature for 7 hours. The resulting mixture was evaporated in vacuo and diluted with EtOAc. The organic solution was washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-60:40) to give ethyl (4-hydroxy-1H-indol-1-yl)acetate.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additiondiluted with EtOAc
  3. washThe organic solution was washed successively with water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-60:40)

Sources & evidence

ORD record
ord-b279b5fd81ec47d6a6ba3ed1f7bf7ed4
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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