Pyridine → HCID 23374178, compound

HRID 865615Notes

Reaction equation

HRID 865615 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 colourless oil. 1H NMR (60 MHz, CDCl3): 6 0.88 (m, 3H, CH3CH2), 1.30 (m, 28H, CH2), 2.20 (m, 6H, CH2), 3.65 (s, 14H, 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-c571b36613054abea60a27a591454931
Source dataset
uspto-grants-1996_10
Patent number
US05567413

Reaction notes

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