HCID 15708221, compound → HCID 54098979, compound

HRID 374718Notes

Reaction equation

HRID 374718 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C@@H:11]([OH:14])CO)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+]>CO>[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[CH:11]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15708221HCID 15708221, compoundHCID 23667635Sodium periodate

Product 1

HCID 54098979HCID 54098979, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

740 mg of (2R,3R)-4-benzyloxy-3-(1-naphthylmethyl)butan-1,2-diol was dissolved in 50 ml of methanol, and 19 ml of an aqueous solution of 568 mg of sodium metaperiodate was added thereto under stirring at 0° C. The mixture was stirred at room temperature for 4 hours. The insolubles were removed by filtration, and then the solvent was concentrated under reduced pressure. The residue was diluted with a saturated sodium hydrogencarbonate aqueous solution, and extracted with diethyl ether. Then, the extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. 620 mg of (2R)-3-benzyloxy-2-(1-naphthylmethyl)-1-propanal thereby obtained as oily substance, was dissolved in 50 ml of acetone, and Jones' reagent was added thereto under stirring at 0° C. The mixture was stirred at the same temperature for 1.5 hours. To the reaction solution, isopropanol was added for decomposition of the reagent. Then, the insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure. The concentrated solution was diluted with ethyl acetate, washed sequentially with water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1 ) to obtain 457 mg of the above identified compound as colorless oily substance.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. customThe insolubles were removed by filtration
  3. concentrationthe solvent was concentrated under reduced pressure
  4. additionThe residue was diluted with a saturated sodium hydrogencarbonate aqueous solution
  5. extractionextracted with diethyl ether
  6. washThen, the extract was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-629cc7fd68064cedb314457f58b92da6
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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