Tetrabutylammonium Fluoride → HCID 86718427, compound

HRID 2273307Notes

Reaction equation

HRID 2273307 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:33]2[CH:37]=[CH:36][O:35][N:34]=2)[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[O:35]1[CH:36]=[CH:37][C:33]([C:22]2[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=[C:20]([CH2:19][OH:18])[N:21]=2)=[N:34]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90122536HCID 90122536, compound

Product 1

HCID 86718427HCID 86718427, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound obtained in step (2) (6.22 g) was dissolved in THF (200 ml), TBAF (a 1.0 M THF solution, 11.6 ml) was added under stirring, and stirring was conducted for 4 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by flash chromatography (ethyl acetate/hexane=50%→100%) using an amino column (trade name: Hi-Flash Column 3L Amino, manufactured by Yamazen Corporation) to give the title compound (1.61 g).

Workup

  1. stirringstirring
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by flash chromatography (ethyl acetate/hexane=50%→100%)

Sources & evidence

ORD record
ord-acfbea01fdcc4c5580e04748adbdc0a3
Source dataset
uspto-grants-2015_09
Patent number
US09120835B2

Reaction notes

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