Water → HCID 57567586, compound

HRID 1727858Notes

Reaction equation

HRID 1727858 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH: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)[OH:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:41](OC(=O)C)(=[O:43])[CH3:42].O>CN(C)C=O.C(OCC)(=O)C>[C:41]([O:12][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=1)[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)=[CH:17][CH:18]=1)(=[O:43])[CH3:42]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23022688HCID 23022688, compound

Product 1

HCID 57567586HCID 57567586, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Tert-butylphenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]-methanol (51 mg) was dissolved in N,N-dimethylformamide (10 ml). Triethylamine (1 ml) and acetic anhydride (0.5 ml) were then added to the solution, and the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and was dried over sodium sulfate. The solvent was removed by evaporation under the reduced pressure, and the residue was purified by thin-layer chromatography on silica gel using chloroform/acetone for development to give the title compound (35 mg, yield 63%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was removed by evaporation under the reduced pressure
  5. customthe residue was purified by thin-layer chromatography on silica gel

Sources & evidence

ORD record
ord-6d6d10ba37b0436d91598dba9746e9b5
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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