Tetrabutylammonium Fluoride → 5-Azido-3,3-dimethyl-pentan-1-ol

HRID 1807006Notes

Reaction equation

HRID 1807006 reaction equation
[N:1]([CH2:4][CH2:5][C:6]([CH3:18])([CH3:17])[CH2:7][CH2:8][O:9][Si](C(C)(C)C)(C)C)=[N+:2]=[N-:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[N:1]([CH2:4][CH2:5][C:6]([CH3:18])([CH3:17])[CH2:7][CH2:8][OH:9])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86640424(5-Azido-3,3-dimethyl-pentyloxy)-tert-butyl-dimethyl-silane

Product 1

HCID 866404255-Azido-3,3-dimethyl-pentan-1-olYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Step C To a solution of (5-azido-3,3-dimethyl-pentyloxy)-tert-butyl-dimethyl-silane (0.8 g, 3 mmol) in tetrahydrofuran (5 mL) was added tetrahydrofuran solution (1 M, Aldrich) of TBAF (4.9 mL, 4.9 mmol). The reaction mixture was stirred at room temperature for 1 h. The mixture was concentrated, the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:3) to give 5-azido-3,3-dimethyl-pentan-1-ol as a colorless oil (0 g, 76%)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:hexanes=1:3)

Sources & evidence

ORD record
ord-7ce845b6bd97486c9b95214c9a496ce6
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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