Phosphate → 2-(4-((Tert-butyldimethylsilyl)oxy)phenyl)ethan-1-ol

HRID 916824Notes

Reaction equation

HRID 916824 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].P([O-])([O-])([O-])=O>C1COCC1>[Si:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][OH:3])=[CH:7][CH:8]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 10393TyrosolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112882212-(4-((Tert-butyldimethylsilyl)oxy)phenyl)ethan-1-olYield 71.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 145 mg) was added portionwise to a solution of 4-(2-hydroxyethyl)phenol (502 mg) in THF (15 ml) and the mixture was stirred at 20° C. for 30 min. tert-Butyldimethylsilyl chloride (547 mg) was added and the mixture was stirred for 75 min. Phosphate buffer solution (pH 6.5) was added and the mixture was extracted with EtOAc. The combined extracts were dried (Na2SO4) and the solvent evaporated in vacuo to give a residue which was purified by SPE (10 g). Elution with DCM-cyclohexane (1:3) then DCM then EtOAc gave the title compound (658 mg). LCMS RT=3.62 min.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent evaporated in vacuo
  5. customto give a residue which
  6. customwas purified by SPE (10 g)
  7. washElution with DCM-cyclohexane (1:3)

Sources & evidence

ORD record
ord-90b23f6043644b9d9eacbfccef726b5f
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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