Trimethyl benzene-1,3,5-tricarboxylate → 2-[3,5-bis-(Methoxycarbonyl)-benzoyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine

HRID 977580Notes

Reaction equation

HRID 977580 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]([C:29]1[CH:34]=[C:33]([C:35](OC)=[O:36])[CH:32]=[C:31]([C:39]([O:41][CH3:42])=[O:40])[CH:30]=1)=[O:28]>O1CCCC1>[CH3:42][O:41][C:39]([C:31]1[CH:32]=[C:33]([CH:34]=[C:29]([C:27]([O:26][CH3:25])=[O:28])[CH:30]=1)[C:35]([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)=[O:36])=[O:40]

Participants

5

Reactant 3

HCID 75881Trimethyl benzene-1,3,5-tricarboxylateHCID 156617082-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl)-pyridineHCID 178418339Butyllithium

Product 1

HCID 156617452-[3,5-bis-(Methoxycarbonyl)-benzoyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridineYield 14.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under the conditions of example 1B, 1 g of 2-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl)-pyridine in 10 ml of tetrahydrofuran is mixed with 4.26 ml of n-butyllithium (1.6 molar in hexane) and 807 mg of 1,3,5-benzenetricarboxylic acid trimethylester in 6 ml of tetrahydrofuran, worked up and chromatographed on silica gel with hexane/ethyl acetate=95/5 to 75/25. 203 mg of oily crude product is obtained, which is subjected to complete purification of the high-pressure liquid chromatography on silanized silica gel (RP 18 material) with methanol/H2O=9:1. 74 mg of the title compound is thus obtained as colorless oil.

Workup

  1. customchromatographed on silica gel with hexane/ethyl acetate=95/5 to 75/25

Sources & evidence

ORD record
ord-84a82c3d00f145caa040e5be239d769d
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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