Tetrabutylammonium Fluoride → Methyl 2-(2-hvdroxyethyl)indole-5-acetate

HRID 1057797Notes

Reaction equation

HRID 1057797 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([CH2:20][C:21]([O-:23])=[O:22])=[CH:15][CH:14]=2)(C(C)(C)C)(C)C.[F-].[CH2:25]([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH2:10][C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([CH2:20][C:21]([O:23][CH3:25])=[O:22])=[CH:15][CH:14]=2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317218742-(t-Butyldimethylsilyl-oxyethyl)-indole-5-acetate

Product 1

HCID 15462903Methyl 2-(2-hvdroxyethyl)indole-5-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 2-(2-(t-butyldimethylsilyl-oxyethyl)-indole-5-acetate (400 mg; 1.15 mmol) in ca. 4 ml of THF was added a 1 M tetrabutylammonium fluoride in THF (1.2 mL; 1.05 eq) at 0° C. After 15 minutes, the reaction was allowed to warm to room temperature and stirred for an additional 3 hours. It was concentrated, diluted with water and extracted with ethyl acetate. The organic layer was washed with water, dried (Na2SO4), concentrated and chromatographed (silica gel, hexane:ethyl acetate 4:1) to yield 241 mg of the title compound as a colorless oil.

Workup

  1. concentrationIt was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed (silica gel, hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-d87c3cd0282945ca9035be69b2a6e2b7
Source dataset
uspto-grants-2003_02
Patent number
US06515015B1

Reaction notes

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