Trifluoromethanesulfonic acid → HCID 54241444, compound

HRID 728746Notes

Reaction equation

HRID 728746 reaction equation
[OH:1][CH:2]([CH2:34][CH2:35]CCCCCCCCCCCCC)[CH:3]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]CCCC)[C:4]([O:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])=[O:5].ClC(Cl)(Cl)C(=N)O[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[CH2:53]([O:1][CH:2]([CH2:34][CH2:35][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:3][CH2:2][CH2:34][CH3:35])[CH:3]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:4]([O:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])=[O:5])[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 53715896HCID 53715896, compound

Product 1

HCID 54241444HCID 54241444, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Then, phenacyl 3-hydroxy-2-n-octadecyl-octadecanoate (IV) (1.81 g, 2.94 millimole) was dissolved in dry methylene chloride (80 ml) under, argon atmosphere, and benzyl 2,2,2-trichloro-acetimidate (0.66 ml, 3.53 millimole) and trifluoromethane sulfonic acid (0.052 ml, 0.59 millimole) were successively added dropwise thereto with ice cooling. The reaction mixture was allowed to warm to room temperature, and to react for 17 hours, then methylene chloride was added to the reaction mixture, and the obtained solution was successively washed with saturated aqueous sodium bicarbonate solution and water, and then dried over anhydrous sodium sulfate. The solvent was distilled off from the solution. The residue was dissolved in a developing solvent (benzene:n-hexane=6:4), and fractionated through silicagel column (benzene:n-hexane=6:4), and the fast eluting fractions comprising impurities were discarded and then the later colorless fractions were pooled and the solvent was distilled off to give phenacyl 3-benzyloxy-2-n-tetradecyl-octadecanoate (V) (783.9 mg) in the form of colorless oil.

Workup

  1. additionwere successively added dropwise
  2. customto react for 17 hours
  3. washthe obtained solution was successively washed with saturated aqueous sodium bicarbonate solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off from the solution
  6. dissolutionThe residue was dissolved in a developing solvent (benzene:n-hexane=6:4)
  7. washthe fast eluting fractions
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-02cf8530d272432aa58ac3df54a3f8b7
Source dataset
uspto-grants-1991_09
Patent number
US05049664

Reaction notes

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