Water → (5RS)-5-Hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentanoic acid methyl ester

HRID 1756321Notes

Reaction equation

HRID 1756321 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[CH:10]([OH:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:3]=1.C([Li])CCC.[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH:31]=[O:32].O>O1CCCC1.ClCCl>[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH:31]([OH:32])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[CH:10]([OH:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 554053Pentanoic acid, 5-oxo-, methyl esterHCID 156617082-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl)-pyridineHCID 178418339Butyllithium

Product 1

HCID 15661711(5RS)-5-Hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 326 mg of 2-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine in 5 ml of tetrahydrofuran is mixed with 1.25 ml of n-butyllithium (1.6 molar in hexane) at -78° C. with stirring and under argon atmosphere. After 10 minutes, a solution of 5-oxo-pentanoic acid methyl ester in 1 ml of tetrahydrofuran is added at -78° C. and stirred for 2 hours at this temperature. The reaction mixture is mixed with water, shaken out with dichloromethane, dried on sodium sulfate, concentrated by evaporation and the crude product is chromatographed on silica gel with hexane/ethyl acetate 98/2. 188 mg of the title compound is thus obtained as colorless oil.

Workup

  1. stirringstirred for 2 hours at this temperature
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customthe crude product is chromatographed on silica gel with hexane/ethyl acetate 98/2

Sources & evidence

ORD record
ord-ef8b9f87929543a9a5ffa906a0e8a900
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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