Tetrabutylammonium Fluoride → Indole

HRID 1095506Notes

Reaction equation

HRID 1095506 reaction equation
C1([C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)CC1.C1(C2C3C(=CC=CC=3)NC=2[Si](C)(C)C)CC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 57475132HCID 57475132, compoundHCID 66783170HCID 66783170, compound

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

3-Cyclopropyl-1H-indole (Ind-11) 3-Cyclopropyl-2-trimethylsilanyl-1H-indole (1.56 g, 6.0 mmol)) was dissolved in tetrahydrofuran (40 ml), tetrabutylammonium fluoride×3H2O (2.79 g, 8.84 mmol) was added and the mixture was stirred at 70° C. for 2 h. The reaction mixture was concentrated, water (90 ml) and diethyl ether (70 ml) were added and the mixture was stirred for 10 min. The phases were separated. The aqueous phase was extracted with diethyl ether (2×50 ml). The combined organic phases were dried with sodium sulfate and concentrated. Ind-11 was isolated as a brown oil in a yield of 99% (1.04 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (90 ml) and diethyl ether (70 ml) were added
  3. stirringthe mixture was stirred for 10 min
  4. customThe phases were separated
  5. extractionThe aqueous phase was extracted with diethyl ether (2×50 ml)
  6. dry with materialThe combined organic phases were dried with sodium sulfate
  7. concentrationconcentrated
  8. customInd-11 was isolated as a brown oil in a yield of 99% (1.04 g)

Sources & evidence

ORD record
ord-0999cfcde58d4a668b07c1fc1501e372
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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