Tetrabutylammonium Fluoride → HCID 58522476, compound

HRID 1946638Notes

Reaction equation

HRID 1946638 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[O:14][C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[O:14][C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59783839HCID 59783839, compound

Product 1

HCID 58522476HCID 58522476, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Title compound 461 (4.29 g, 11.6 mmol) was dissolved in THF (30.0 mL) and tetrabutylammonium fluoride (1M in THF, 13.4 mL, 13.4 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour. The mixture was evaporated to ⅓ of the volume and then poured in ether. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography (50-70% ethyl acetate in hexanes) to afford title compound 462 (2.51 g, 85%) as a white solid. MS (m/z): 256.1 (M+H).

Workup

  1. customThe mixture was evaporated
  2. additionpoured in ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified by flash chromatography (50-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-33d112d2503d4fabafda08e2a779189f
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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