Tetrabutylammonium Fluoride → HCID 72546338, compound

HRID 2280083Notes

Reaction equation

HRID 2280083 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[C:25]2[C:20](=[C:21]([N:26]([CH3:28])[CH3:27])[CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]2[CH2:29][CH2:30][CH2:31][C:17]=12)=[O:15])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:28][N:26]([CH3:27])[C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[CH:19]=[C:18]1[CH2:29][CH2:30][CH2:31][C:17]1=[C:16]2[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 72546337HCID 72546337, compound

Product 1

HCID 72546338HCID 72546338, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An oven-dried 25 mL one-necked round-bottomed flask was charged with compound 12 (0.040 g, 0.091 mmol) and THF (15 mL). TBAF (0.18 mL of a 1.0 M THF solution, 0.18 mmol) was added and the mixture was stirred at rt for 3 h. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 1:1). The solution was then concentrated under reduced pressure and the reaction residue was purified by silica gel flash column chromatography, eluting with AcOEt/n-hexane 6:4, to provide 0.027 g of the title compound as a yellow oil in a 91% yield.

Workup

  1. customThe consumption of the starting material
  2. concentrationThe solution was then concentrated under reduced pressure
  3. customthe reaction residue was purified by silica gel flash column chromatography
  4. washeluting with AcOEt/n-hexane 6:4

Sources & evidence

ORD record
ord-099e1582197f45608aeb782fa026b5b5
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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