Tetrabutylammonium Fluoride → Di-tert-butyl 4-hydroxy-2,2-dimethylbutyl phosphate

HRID 2238328Notes

Reaction equation

HRID 2238328 reaction equation
[P:1]([O:13][CH2:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH2:17][O:18][Si](C(C)(C)C)(C)C)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[P:1]([O:13][CH2:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH2:17][OH:18])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86616510Di-tert-butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutyl phosphate

Product 1

HCID 86616511Di-tert-butyl 4-hydroxy-2,2-dimethylbutyl phosphateYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Example 10B (0.435 g, 1.03 mmol) in THF (3.8 mL) was added a solution of tetrabutylammonium fluoride in THF (1 M, 1.2 mL), and the reaction was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 33% ethyl acetate in hexane, to give the title compound (0.239 g, 75%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with 33% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5006fedb61904efea982695659e2c539
Source dataset
uspto-grants-2010_05
Patent number
US07718633B2

Reaction notes

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