Tetrabutylammonium Fluoride → HCID 21468968, compound

HRID 866244Notes

Reaction equation

HRID 866244 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:6][O:5][C:4]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=2[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=[CH:18]3)=[N:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1([CH3:34])[CH2:6][O:5][C:4]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=2[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[CH:18]3)=[N:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21468835HCID 21468835, compound

Product 1

HCID 21468968HCID 21468968, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4,4-dimethyl-2-[2-(1-triisopropylsilylindol-5-yl)-6-methoxyphenyl]-2-oxazoline (8.5 g, 17.8 mmoles) was dissolved in 300 ml of THF. The solution was cooled to 0° C. Tetrabutylammonium fluoride (17.8 mmoles, 178 ml of 1M in THF) was added dropwise. The reaction was stirred at 0°-5° C. for 40 minutes, poured into ice water, and extracted into ether. The organic phase was dried over sodium sulfate, and the solvent was removed. The reaction produced 5.7 g of 4,4-dimethyl-2-[2-(indol-5-yl)-6-methoxyphenyl]-2-oxazoline. (MS)

Workup

  1. extractionextracted into ether
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-80fa0fef657d4c0091677e5018722042
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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