Water → HCID 14349129, compound

HRID 414833Notes

Reaction equation

HRID 414833 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.Br[CH2:13][C:14]1[S:18][C:17]([CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=1.[OH-].[Na+].O>CS(C)=O>[OH:25][CH:19]([C:17]1[S:18][C:14]([CH2:13][O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:15][CH:16]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21280567HCID 21280567, compoundHCID 178516385quinolin-4-ol

Product 1

HCID 14349129HCID 14349129, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a well-stirred solution of 4-hydroxyquinoline (2 g, 0.014 mol) and 5-bromomethyl-2-(1-hydroxyhexyl)thiophene (3.82 g, 0.014 mol) in DMSO (50 ml) was added a 2N solution of sodium hydroxide (8 ml, 0.016 mol). The mixture became warm immediately. This clear solution was stirred overnight at room temperature, and then was poured into water (200 ml). The aqueous solution was extracted thoroughly with ethyl acetate (4×30 ml). The organic extract was washed with water and brine, and then dried over MgSO4. All volatiles were removed, and the crude product was purified chromatographically (silica gel; 15% ethyl acetate in hexane) to yield 2.1 g (44%) of the pure product.

Workup

  1. temperatureThe mixture became warm immediately
  2. extractionThe aqueous solution was extracted thoroughly with ethyl acetate (4×30 ml)
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over MgSO4
  6. customAll volatiles were removed
  7. customthe crude product was purified chromatographically (silica gel; 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e41b11b8b0174f1581723ad8da5f7d79
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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