Pyridine → HCID 23374178, compound

HRID 1871828Notes

Reaction equation

HRID 1871828 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].N1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[C:21]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])(=[O:20])[CH2:22][CH2:23][CH2:24][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:19]#[C:18][C:17]#[C:16][CH2:15][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 8200Tetraethylene Glycol

Product 1

HCID 23374178HCID 23374178, compoundYield 41%

Procedure

10,12-Tricosadiynoic acid (2.50 g, 0.007 mol) in tetrahydrofuran (30 ml) was reacted with oxalyl chloride (2.25 g, 0.017 mol) to obtain the corresponding acid chloride. This acid chloride (2.45 g, 0.007 mol) dissolved in anhydrous tetrahydrofuran (10 ml) was added dropwise to a mixture of tetraethylene glycol (1.32 g, 0.007 mol) and anhydrous pyridine (0.83 g, 0.01 mol) in anhydrous tetrahydrofuran (40 ml). The mixture was stirred overnight at room temperature. The precipitated pyridinium salt was filtered off and the solvent removed under vacuum. The resulting liquid was purified by flash chromatography (silica gel/ethyl acetate) to give 1.50 g (41%) of the title compound as a colour less oil. 1H NMR (60 MHz, CDCl3): δ 0.88 (m, 3H, CH3CH2), 1.30 (m, 28H, CH2), 2.20 (m, 6H, CH2), 3.65 (s, 11H, 7×CH2O), 4.20 (m, 2H, CH2CO).

Workup

  1. filtrationThe precipitated pyridinium salt was filtered off
  2. customthe solvent removed under vacuum
  3. customThe resulting liquid was purified by flash chromatography (silica gel/ethyl acetate)

Sources & evidence

ORD record
ord-24a3d2e83e314596941d4c46908ff37c
Source dataset
uspto-grants-2000_08
Patent number
US06106806

Reaction notes

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