Trityl chloride → HCID 21288382, compound

HRID 868448Notes

Reaction equation

HRID 868448 reaction equation
[CH3:1][CH:2]([CH3:23])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH:19]([OH:22])[CH2:20][OH:21].[C:24](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:24]([O:21][CH2:20][CH:19]([OH:22])[CH2:18][O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:23])[CH3:1])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 21288381HCID 21288381, compound

Product 1

HCID 21288382HCID 21288382, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.0 g (6.06 mmole) of 1-(15-methylhexadecyloxy)-2,3-propanediol, 2.54 g (9.09 mmole) of trityl chloride and 20 ml of pyridine was stirred at room temperature for 2 days, and then pyridine was distilled off. To the residue was added 50 ml of ethyl acetate and the ethyl acetate solution was washed with 1N hydrochloric acid, water and saturated sodium bicarbonate solution, in order, and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (100 g) and eluted with hexane-ethyl acetate (20:1) to give 2.3 g of crude 1-(trityloxy)-3-(15-methylhexadecyloxy)-2-propanol. This product was treated by following the procedure of that of Reference Example 12 to give 1.0 g (yield: 39%) of the desired product.

Workup

  1. distillationpyridine was distilled off
  2. additionTo the residue was added 50 ml of ethyl acetate
  3. washthe ethyl acetate solution was washed with 1N hydrochloric acid, water and saturated sodium bicarbonate solution, in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccating agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washeluted with hexane-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-520a4a3c75de4716b9adabd8a03b770e
Source dataset
uspto-grants-1988_10
Patent number
US04778912

Reaction notes

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