Water → 2-(4-Hydroxybutyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole

HRID 65031Notes

Reaction equation

HRID 65031 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7][C:8]1[S:9][C:10]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:12]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:2][CH2:3][CH2:5][CH2:6][CH2:7][C:8]1[S:9][C:10]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 202350322-(3-Methoxycarbonylpropyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 202350252-(4-Hydroxybutyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazoleYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran was dissolved 770 mg of 2-(3-methoxycarbonylpropyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole prepared by example 4, which was then cooled with ice. To the solution was added little by little 100 mg of lithium aluminium hydride, which was stirred for one hour. To the mixture was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated, followed by purifying by means of a silica-gel chromatography [chloroform-methanol (9:1)] to yield 576 mg (81%) of 2-(4-hydroxybutyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole as an oily substance.

Workup

  1. temperaturewas then cooled with ice
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customby purifying by means of a silica-gel chromatography [chloroform-methanol (9:1)]

Sources & evidence

ORD record
ord-cc4cb1a824a34e5bb88ae521579aea3e
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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