Ethanol → HCID 23022688, compound

HRID 1727857Notes

Reaction equation

HRID 1727857 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].B.[Na].C(O)C>O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:17][CH:18]=2)[OH:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 9932979HCID 9932979, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 23022688HCID 23022688, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[4-(Tert-butyl)phenyl]{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-methanone (111 mg) and sodium boron hydride (76 mg) were added to ethanol (15 ml), and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. Chloroform was removed by evaporation under the reduced pressure to give a crude which was then purified by thin-layer chromatography on silica gel using chloroform/ethyl acetate for development to give (4-tert-butylphenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]methanol (108 mg, yield 97%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  3. customChloroform was removed by evaporation under the reduced pressure
  4. customto give a crude which
  5. customwas then purified by thin-layer chromatography on silica gel

Sources & evidence

ORD record
ord-38b38a2dcd8e48be9b68f0547770587c
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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