Stearyl Alcohol → HCID 19593947, compound

HRID 612341Notes

Reaction equation

HRID 612341 reaction equation
[CH2:1](O)[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][CH2:15][CH2:16][CH2:17][CH3:18].[CH:20](N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:44]1([C:50]2[CH:51]=[CH:52][C:53]3[O:57][CH:56]=[N:55][C:54]=3[CH:58]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(Cl)(Cl)Cl>[CH2:20]=[C:56]1[N:55]([CH2:1][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][CH2:15][CH2:16][CH2:17][CH3:18])[C:54]2[CH:58]=[C:50]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:51]=[CH:52][C:53]=2[O:57]1

Participants

6

Reactant 4

HCID 8221Stearyl AlcoholHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 33092485-phenylbenzoxazole

Product 1

HCID 19593947HCID 19593947, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Powdered 1-octadecanol (15.4 g, 56.9 mmol) and diisopropylethylamine (9.9 mL, 56.9 mmol) are dissolved in 200 mL CHCl3 (dried over molecular sieves). To the above stirred solution is added trifluoromethanesulfonic anhydride (10.4 mL) dropwise over a period of 1 hours. Powdered 5-phenylbenzoxazole (16.7 g, 79.7 mmol) is then added portion-wise over a period of 10 minutes. After stirring overnight, the solution is washed with water and dried with anhydrous Na2SO4. The solution is loaded onto a large silica column and eluted with MeOH/CHCl3. The product is obtained as a colorless solid (20 g, 77%).

Workup

  1. washthe solution is washed with water
  2. dry with materialdried with anhydrous Na2SO4
  3. washeluted with MeOH/CHCl3

Sources & evidence

ORD record
ord-aed24100fa3d42ac8f9dbd85f7f67011
Source dataset
uspto-grants-1999_12
Patent number
US06004536

Reaction notes

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