Tetrabutylammonium Fluoride → HCID 90266379, compound

HRID 1483174Notes

Reaction equation

HRID 1483174 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C@@H:11]([CH2:13][O:14][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[O:10][C:9]2=[O:32])=[N:6][CH:7]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C@@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:32])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90266380HCID 90266380, compound

Product 1

HCID 90266379HCID 90266379, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 25b (1.4 g, 2.83 mmol) was dissolved in tetrahydrofuran, cooled to 0° C., and nBu4NF (4.2 mL, 4.2 mmol, 4.2 M solution in tetrahydrofuran) was added. The mixture was allowed to react for 5 hrs and monitored by TLC. After the reaction completed, the mixture was diluted with water, and extracted with ethyl acetate. The organic phase was wash with saturated saline solution, dried over anhydrous sodium sulfate. Column chromatography afforded 645 mg of white solid, yield 83%.

Workup

  1. customto react for 5 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was wash with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-01be3988d68649e598c49ca9811b7eef
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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