Water → HCID 19069065, compound

HRID 1957299Notes

Reaction equation

HRID 1957299 reaction equation
N1C2C(=CC=CC=2)C=CC=1COC1C=CC([C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:23][CH:22]=2)=O)=CC=1.[C:39]1([Li])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[OH2:46]>C1COCC1>[N:30]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:37]=[CH:38][C:29]=1[CH2:28][O:46][C:39]1[CH:44]=[CH:43][C:42]([C:25]2[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)=[CH:25][CH:26]=3)=[C:23]([CH2:24][OH:27])[CH:22]=[CH:21][CH:26]=2)=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10505429HCID 10505429, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 19069065HCID 19069065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-quinolylmethoxy)phenyl ketone (0.520 g, 1.05 mmol) in anhydrous THF (10 mL) at -78° C. phenyl lithium (0.873 mL, 1.57 mmol) was added and the reaction mixture was allowed to warm to room temperature. Water was then added to the reaction mixture and the product was extracted with EtOAc (233 ). The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with Et2O to give 400 mg of (bis(4-(2-quinolylmethoxy)phenyl)-phenyl)methanol as a cream solid.

Workup

  1. extractionthe product was extracted with EtOAc (233 )
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-3039efe2f7f045208a09663507620a7f
Source dataset
uspto-grants-1998_07
Patent number
US05783586

Reaction notes

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