Pyridine → 2-Benzoyl-3-octadecyl-1-tritylglycerol

HRID 986187Notes

Reaction equation

HRID 986187 reaction equation
[C:1]([O:20][CH2:21][CH:22]([CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:50](Cl)(=[O:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>ClCCl>[C:50]([O:23][CH:22]([CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:21][O:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Product 1

HCID 540774532-Benzoyl-3-octadecyl-1-tritylglycerolYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 200 ml of dried dichloromethane was dissolved 32.0 g (53.4 mmole) of 1-trityl-3-octadecylglycerol, and 22.4 ml of dried pyridine and then a solution of 6.7 ml (57.9 mmole) of benzoyl chloride in 100 ml of dried dichloromethane were added dropwise to the solution under stirring at 0° to 3° C. over the period of time of 30 minutes. The reaction mixture was stirred at room temperature for another 2 hours, and then concentrated under reduced pressure. 200 ml of ether was added to the residue, and the insoluble material was filtered off. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 28.8 g (7%) of 2-benzoyl-3-octadecyl-1-tritylglycerol as an oily material.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 2 hours
  2. concentrationconcentrated under reduced pressure
  3. addition200 ml of ether was added to the residue
  4. filtrationthe insoluble material was filtered off
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-e4d5047fbcfc4a4485847e28be323c89
Source dataset
uspto-grants-1987_12
Patent number
US04710579

Reaction notes

Loading…