Triethylamine → 1-Hydroxy-3-(z-15-tetracosenoyloxy)propane

HRID 432973Notes

Reaction equation

HRID 432973 reaction equation
[C:1](Cl)(=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[CH2:27]([OH:31])[CH2:28][CH2:29][OH:30].C(N(CC)CC)C>C(Cl)Cl>[OH:30][CH2:29][CH2:28][CH2:27][O:31][C:1](=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104421,3-PropanediolHCID 11199988Nervonoyl chloride

Product 1

HCID 591186921-Hydroxy-3-(z-15-tetracosenoyloxy)propane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of z-15-tetracosenoyl chloride, prepared according to Description 1, (0.129 mol, 49.7 g) in methylene chloride (500 mL) was added dropwise (over a period of 2.5-3 h) to a mixture of propane-1,3-diol (0.780 mol, 58.9 g) and triethylamine (0.323 mol, 32.6 g) in methylene chloride (1200 mL) at 0° C. under nitrogen. The mixture was left stirring in the ice bath for another 2 h, until TLC (80:18:2 petroleum ether-ethyl ether-acetic acid) showed that the by-product of the reaction started to form (Rf product: 0.16; by-product: 0.63). The solution was washed with 2M sulphuric acid (2×150 mL), saturated sodium bicarbonate (3×300 mL) and saturated sodium chloride (2×300 mL). It was finally dried over anhydrous sodium sulphate, concentrated and purified by flash chromatography on silica gel (7:3 petroleum ether-ethyl ether) to yield 1-hydroxy-3-(z-15-tetracosenoyloxy)propane as a white solid.

Workup

  1. additionwas added dropwise (over a period of 2.5-3 h)
  2. waitThe mixture was left
  3. customto form (Rf product: 0.16; by-product: 0.63)
  4. washThe solution was washed with 2M sulphuric acid (2×150 mL), saturated sodium bicarbonate (3×300 mL) and saturated sodium chloride (2×300 mL)
  5. dry with materialIt was finally dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. custompurified by flash chromatography on silica gel (7:3 petroleum ether-ethyl ether)

Sources & evidence

ORD record
ord-99043501cdbe43e186ca9e7da3b13ee6
Source dataset
uspto-grants-2003_12
Patent number
US06664406B1

Reaction notes

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