Phenol → HCID 21697025, compound

HRID 379020Notes

Reaction equation

HRID 379020 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]I)=[CH:10][CH:9]=1.[C:23]([O-:26])([O-])=[O:24].[Cs+].[Cs+].C[N:30]([CH3:33])C=O>CCOC(C)=O>[C:33]([C:3]1[CH:4]=[CH:5][C:6]([C:23]([O:26][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:24])=[C:1]([O:7][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9][CH:10]=2)[CH3:15])[CH:2]=1)#[N:30]

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 19702263HCID 19702263, compound

Product 1

HCID 21697025HCID 21697025, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a phenol, as described in Step A, in 5 mL of dimethyl formamide (DMF) was added biphenyl-4-ylethyl iodide (170 mg, 0.55 mmol) and Cs2CO3 (246 mg, 0.75 mmol). The suspension was stirred for 16 hr. After this time, the reaction mixture was diluted with EtOAc, extracted with water (3×), washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2; hexane:EtOAc 9:1 then 4:1) to provide the title compound.

Workup

  1. extractionextracted with water (3×)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2

Sources & evidence

ORD record
ord-c40e56d4ed224c668e20c8c1715251d7
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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