Sulfuric Acid → HCID 86660596, compound

HRID 2367949Notes

Reaction equation

HRID 2367949 reaction equation
[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:18](O)[CH:19]=[CH2:20].OS(O)(=O)=O>>[CH2:20]([C:2]([C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4])=[O:1])[CH:19]=[CH2:18]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 24436Sodium SulfateHCID 66308D-Arabinose

Product 1

HCID 86660596HCID 86660596, compoundYield 60%

Conditions

Temperature
85 °C

Procedure

D-Arabinose (100 g, 666 mmol) and Na2SO4 (100 g, 703 mmol) were suspended in allyl alcohol (1 L, 14.65 mol) at room temperature; to this suspension was added concentrated H2SO4 (10.4 mL, 187 mmol). The reaction was stirred at 85° C. for 12 h, filtered, and the precipitate was washed with allyl alcohol (2 times 300 mL). The combined filtrates were concentrated in vacuo and purified by silica gel flash chromatography (DCM to 4:1 DCM:MeOH) to give 32 as an off-white solid (75 g, 394 mmol, 60%).

Workup

  1. filtrationfiltered
  2. washthe precipitate was washed with allyl alcohol (2 times 300 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. custompurified by silica gel flash chromatography (DCM to 4:1 DCM:MeOH)

Sources & evidence

ORD record
ord-cc42bc4a7f2046819ee098d8894ef1af
Source dataset
uspto-grants-2014_04
Patent number
US08703723B2

Reaction notes

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