Phenol → HCID 57835888, compound

HRID 731189Notes

Reaction equation

HRID 731189 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Br)[C:17]1[CH:22]=[CH:21]C=[CH:19][CH:18]=1.[C:24](=[O:27])([O-])[O-:25].[Cs+].[Cs+].[OH-].[Na+].C(O)(C(F)(F)F)=O>CN(C=O)C.O>[CH:14]1([CH2:9][CH2:8][O:7][C:1]2[CH:6]=[CH:5][C:4]([C@@H:22]([C:17]#[C:18][CH3:19])[CH2:21][C:24]([OH:25])=[O:27])=[CH:3][CH:2]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

9

Reactant 6

HCID 996PhenolHCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 14798Sodium Hydroxide

Product 1

HCID 57835888HCID 57835888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of phenol (0.18 mmol), 6-halomethyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene (0.2 mmol) or another benzyl chloride or benzyl bromide compound, and cesium carbonate (0.27 mmol) in DMF (2 mL), was/is stirred at room temperature overnight. The reaction mixture was/is diluted with water and extracted into DCM. The separated DCM layer was/is washed with water. The residue obtained after concentration was/is dissolved into THF and MeOH (1 mL each) and treated with 2 M NaOH solution (0.45 mL, 0.9 mmol). The resulting solution was/is further stirred for 16-48 hours at room temperature. The reaction mixture was/is concentrated, and the residue was/is dissolved in a mixture of DMF/ACN (1:4, 5 mL) containing TFA (67 μL, 0.9 mmol). This solution was/is filtered and purified by preparatory HPLC. The solvent was/is evaporated by freeze-drying to provide the desired product generally as a white amorphous solid.

Workup

  1. extractionextracted into DCM
  2. washThe separated DCM layer was/is washed with water
  3. customThe residue obtained
  4. concentrationafter concentration
  5. dissolutionwas/is dissolved into THF and MeOH (1 mL each)
  6. concentrationThe reaction mixture was/is concentrated
  7. dissolutionthe residue was/is dissolved in a mixture of DMF/ACN (1:4, 5 mL)
  8. filtrationThis solution was/is filtered
  9. custompurified by preparatory HPLC
  10. customThe solvent was/is evaporated
  11. customby freeze-drying

Sources & evidence

ORD record
ord-5dcbbad6fb2a432d99084482bfaf747e
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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