Tetrabutylammonium Fluoride → HCID 59443008, compound

HRID 1959149Notes

Reaction equation

HRID 1959149 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][Si](C(C)(C)C)(C)C)=[CH:15][CH:16]=3)[O:11][C:10]([CH3:27])([CH3:26])[CH:9]=2)=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[O:11][C:10]([CH3:27])([CH3:26])[CH:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59443009HCID 59443009, compound

Product 1

HCID 59443008HCID 59443008, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound obtained in (2) described above (2 g) in tetrahydrofuran (20 mL) was added 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (10 mL) under stirring at 0° C. and the mixture was stirred at the same temperature for 3 hours. The reaction solution was diluted with an aqueous solution of ammonium chloride (50 mL) and extracted with ethyl acetate (30 mL×3). The combined organic layer was dried over sodium sulfate and concentrated in vacuo to give the titled compound (1.5 g) as a brown powder, which was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred at the same temperature for 3 hours
  2. extractionextracted with ethyl acetate (30 mL×3)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c39efe5bee84272b2c5a4c1123714c7
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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