Tetrabutylammonium Fluoride → HCID 19385668, compound

HRID 2399508Notes

Reaction equation

HRID 2399508 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][Si](C(C)(C)C)(C)C)=[C:16]([CH2:28][CH:29]=[CH2:30])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:31])[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH2:28][CH:29]=[CH2:30])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:31])[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19385605HCID 19385605, compound

Product 1

HCID 19385668HCID 19385668, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.519 g (3.48 mmol) of the product of Step F in 8.0 mL of anhydrous THF was added 3.6 mL of a 1.0 M solution of tetra-n-butylammonium fluoride in THF and the reaction mixture was stirred for 2.5 hours at room temperature. The reaction mixture was then evaporated in vacuo and the residual oil was chromatographed on a silica gel flash chromatography column eluted with ethyl acetate. The purified fractions were combined, evaporated and dried in vacuo to afford the title compound.

Workup

  1. customThe reaction mixture was then evaporated in vacuo
  2. customthe residual oil was chromatographed on a silica gel flash chromatography column
  3. washeluted with ethyl acetate
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b9fc9b9fff1043919805fc1a572aff18
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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