Water → HCID 22009839, compound

HRID 322332Notes

Reaction equation

HRID 322332 reaction equation
[H-].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([O-])=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.O>O1CCCC1>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:17][OH:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 166653HydrideHCID 22009787HCID 22009787, compound

Product 1

HCID 22009839HCID 22009839, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylalminium hydride (1M in toluene, 7.2 ml) was added dropwise to a stirred solution of 7-(2-thienyl)-3-quinolinecarboxylate (500 mg) in tetrahydrofuran (30 m) at 0° C. After stirring for 30 min, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4), and concentrated. The residue was purified by silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:2, v/v) 7-(2-thienyl)-3-quinolylmethanol (270 mg, 63%) was obtained. Recrystallization from ethyl acetate-hexane gave yellow prisms, 143-144° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. washFrom the fraction eluted with ethyl acetate-hexane (1:2

Sources & evidence

ORD record
ord-64c540af28ac447a8025e6d81808634b
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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