Benzyl Bromide → HCID 44278819, compound

HRID 1029454Notes

Reaction equation

HRID 1029454 reaction equation
[H-].[Na+].O[C:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:9][CH:8]=1)([OH:6])[CH3:5].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:26]1([CH2:25][O:6][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:9][CH:8]=2)[CH2:5][O:6][CH2:4][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19745915HCID 19745915, compound

Product 1

HCID 44278819HCID 44278819, compound

Procedure

At 0° C., 50% NaH in oil (37 mg) was added portionwise to a solution of 1-hydroxy-1-(4-2(-quinolinylmethoxy)phenyl)ethanol (Step 1) (104 mg) and benzyl bromide (92 mg). Stirring was continued for 18 h and the reaction was quenched with 25% aqueous NH4OAc. The product was extracted with EtOAc, dried over MgSO4 and purified by flash chromatography on silica gel using EtOAc:hexane (1:4) to give the title compound as an oil.

Workup

  1. customthe reaction was quenched with 25% aqueous NH4OAc
  2. extractionThe product was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c8b777d5891841f38ad5f1b4dab512ff
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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