Pentanoic acid, 5-oxo-, methyl ester → HCID 15661754, compound

HRID 1756339Notes

Reaction equation

HRID 1756339 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[CH:12]([OH:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:3]=1.C([Li])CCC.[CH3:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH:33]=[O:34]>O1CCCC1>[CH3:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH:33]([OH:34])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[CH:12]([OH:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:3]=1

Participants

5

Reactant 3

HCID 554053Pentanoic acid, 5-oxo-, methyl esterHCID 15661752HCID 15661752, compoundHCID 178418339Butyllithium

Product 1

HCID 15661754HCID 15661754, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under the conditions of example 1B, 470 mg of 2-bromo-6-[(1E, 3E)-(5RS)-5-hydroxy-1,3-tridecadienyl]-pyridine in 7 ml of tetrahydrofuran is mixed with 1.84 ml of n-butyllithium (1.6 molar in hexane) and 200 mg of 5-oxo-pentanoic acid methyl ester in 1.5 ml of tetrahydrofuran, worked up and chromatographed on silica gel with hexane/ethyl acetate=95/5. 29 mg of the title compound is obtained as colorless oil.

Workup

  1. customchromatographed on silica gel with hexane/ethyl acetate=95/5

Sources & evidence

ORD record
ord-5f8905c935a94385b002d913d29d989a
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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