HCID 11773223, compound → HCID 86757618, compound

HRID 430752Notes

Reaction equation

HRID 430752 reaction equation
[CH2:1]([C:4]1[O:5][C:6]2[C:21](OCC(OC)=O)=[CH:20][CH:19]=[CH:18][C:7]=2[C:8]=1[CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[CH:2]=C.I([O-])(=O)(=O)=[O:29].[Na+].CCCCCC.[C:40]([O:43][CH2:44]C)(=[O:42])[CH3:41]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[OH:29][CH2:2][CH2:1][C:4]1[O:5][C:6]2[C:21]([CH2:41][C:40]([O:43][CH3:44])=[O:42])=[CH:20][CH:19]=[CH:18][C:7]=2[C:8]=1[CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1

Participants

6

Reactant 3

HCID 11773223HCID 11773223, compoundHCID 21226206Ethyl acetate hexaneHCID 23667635Sodium periodate

Product 1

HCID 86757618HCID 86757618, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

Methyl (2-(2-propenyl)-3-(2-tetrahydropyranyloxyethyl)benzofuran-7-yloxy)acetate (0.97 g) and osmium tetroxide (0.07 M solution in t-butyl alcohol, 0.37 ml) were dissolved in dioxane/water (3:1) and the solution was cooled to 0° C. To this solution, sodium periodate (1.38 g) was added for 10 minutes. After stirring the reaction solution at 0° C. for 30 minutes, the solution was stirred at room temperature for additional 30 minutes. The reaction solution was filtered through Celite and the precipitate was washed with THF (12 ml). The filtrate was cooled to 0° C. and sodium borohydride (98 mg) was added, followed by stirring the resultant for 40 minutes. The reaction solution was poured into water (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1)using silica gel to obtain the desired compound (412 mg, yield: 42%).

Workup

  1. stirringthe solution was stirred at room temperature for additional 30 minutes
  2. filtrationThe reaction solution was filtered through Celite
  3. washthe precipitate was washed with THF (12 ml)
  4. temperatureThe filtrate was cooled to 0° C.
  5. additionsodium borohydride (98 mg) was added
  6. stirringby stirring the resultant for 40 minutes
  7. additionThe reaction solution was poured into water (50 ml)
  8. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  9. washwashed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  10. dry with materialby drying the resultant over sodium sulfate
  11. customAfter removing the sodium sulfate
  12. filtrationby filtration
  13. customthe solvent was removed under reduced pressure
  14. customthe residue was purified by column chromatography (solvent

Sources & evidence

ORD record
ord-e1d9f26aea3749579edec0a9fb2fe5c6
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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