Methyl 3-formylbenzoate → 2-[(1RS)-1-Hydroxy-1-(3-methoxycarbonylphenyl)-methyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine

HRID 977568Notes

Reaction equation

HRID 977568 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:36])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]=[O:35])[CH:29]=1>>[OH:35][CH:34]([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:30]1[CH:31]=[CH:32][CH:33]=[C:28]([C:27]([O:26][CH3:25])=[O:36])[CH:29]=1

Participants

4

Reactant 3

HCID 639145Methyl 3-formylbenzoateHCID 156617082-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl)-pyridineHCID 178418339Butyllithium

Product 1

HCID 156617162-[(1RS)-1-Hydroxy-1-(3-methoxycarbonylphenyl)-methyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridineYield 25.5%

Procedure

Under the conditions of example 1B, 326 mg of 2-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine is reacted with 1.38 ml of n-butyllithium (1.6 molar in hexane) and 181 mg of 3-formylbenzoic acid methyl ester (J. Org. Chem. 31, 1966, 2585), worked up and chromatographed on silica gel with hexane/ethyl acetate 8/2. 105 mg of the title compound is obtained as colorless oil.

Workup

  1. customchromatographed on silica gel with hexane/ethyl acetate 8/2

Sources & evidence

ORD record
ord-a8063f5cd9c8453c96cd94b232c273f7
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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