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

HRID 2288871Notes

Reaction equation

HRID 2288871 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.O>[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

5

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 2

HCID 962WaterSolventHCID 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 con-centrated, 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. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel, hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-00737872c46f4f8aaea39f14a8809481
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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