Water → HCID 21468894, compound

HRID 1938593Notes

Reaction equation

HRID 1938593 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([Si](C(C)C)(C(C)C)C(C)C)[CH:17]=[CH:16]3)=[N:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH3:1][C:2]1([CH3:32])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 21468938HCID 21468938, compound

Product 1

HCID 21468894HCID 21468894, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[2-(4,4-Dimethyloxazolin-2-yl)phenyl]-1-triisopropylsilylindole (1.48 mmoles, 661 mg) in 5 ml THF was treated at 0° C. with tetrabutylammonium fluoride (2.22 mmoles, 2.22 ml of 1.0N solution in THF). The solution was stirred for 3 hours, poured into 30 ml water, and extracted with ether. The organic layer was dried and concentrated. The oil was triturated with ether/hexane, and the solid was isolated by filtration. The reaction yielded 320 mg of 5-[2-(4,4-dimethyloxazolin-2-yl)phenyl]indole. (MS)

Workup

  1. extractionextracted with ether
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe oil was triturated with ether/hexane
  5. customthe solid was isolated by filtration

Sources & evidence

ORD record
ord-23e26e513b044a5a99ebde3fb8000772
Source dataset
uspto-grants-1997_12
Patent number
US05693633

Reaction notes

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