Pyridine → HCID 86239094, compound

HRID 2260959Notes

Reaction equation

HRID 2260959 reaction equation
OCC(CO)(CO)CO.N1C=CC=CC=1.CN(C=O)C.[CH3:21][CH:22]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:51])[CH2:40][CH2:41][CH2:42][CH:43]([CH3:50])[CH2:44][CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:23][CH2:24][CH2:25][C:26](OC[C@@H]([C@@H](CO)O)O)=[O:27].C(Cl)[Cl:53]>>[CH3:21][CH:22]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:51])[CH2:40][CH2:41][CH2:42][CH:43]([CH3:50])[CH2:44][CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:23][CH2:24][CH2:25][C:26]([Cl:53])=[O:27]

Participants

6

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8285PentaerythritolHCID 86620072HCID 86620072, compound

Product 1

HCID 86239094HCID 86239094, compound

Procedure

Pentaerythritol (3.81 g), 2.21 g of pyridine, and 120 ml of dry DMF were mixed and dissolved with heating. The product was cooled to room temperature, the solution of 5 g of 5,9,13,17-tetramethyloctadecanoic acid chloride obtained in the step of synthesis of 1-O-(5,9,13,17-tetramethyloctadecanoyl)erythritol [formula (7)] in 5 ml of methylene chloride was added dropwise thereto, and the mixture was then agitated at room temperature for 1 hour. 100 ml of Methylene chloride was added to the resulting reaction solution, the mixture was washed 3 times with saturated saline, and dried over anhydrous sodium sulfate. Following filtration and concentration under reduced pressure, the concentrate was purified by silica gel column chromatography to obtain 2.50 g of mono-O-(5,9,13,17-tetramethyloctadecanoyl)pentaerythritol having the following properties. The purity determined by HPLC analysis was not lower than 99.5%. The results of NMR analysis are as shown below.

Workup

  1. dissolutiondissolved
  2. temperaturewith heating

Sources & evidence

ORD record
ord-29ce66191ae24c26bf33469e54e24ce1
Source dataset
uspto-grants-2010_12
Patent number
US07846903B2

Reaction notes

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