Dimethyl isophthalate → 2-(3-Methoxycarbonylbenzoyl)-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine

HRID 977578Notes

Reaction equation

HRID 977578 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:38])[C:28]1[CH:37]=[CH:36][CH:35]=[C:30]([C:31](OC)=[O:32])[CH:29]=1>O1CCCC1>[CH3:25][O:26][C:27]([C:28]1[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=1)[C:31]([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:32])=[O:38]

Participants

5

Reactant 3

HCID 15088Dimethyl isophthalateHCID 156617082-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl)-pyridineHCID 178418339Butyllithium

Product 1

HCID 156617412-(3-Methoxycarbonylbenzoyl)-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridineYield 15.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under the conditions of example 1B, 652 mg of 2-bromo-6[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine in 3 ml of tetrahydrofuran is mixed with 2.75 ml of n-butyllithium (1.6 molar in hexane) and 427 mg of isophthalic acid dimethyl ester in 3 ml of tetrahydrofuran, worked up and chromatographed on silica gel with hexane/ethyl acetate=95/5 to 75/25. 130 mg of an 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=85/15. 58 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-79b2af50a8a0483ebfbde7e82c7a2998
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

Loading…