Allyl bromide → HCID 54309998, compound

HRID 1111155Notes

Reaction equation

HRID 1111155 reaction equation
[OH:1][C@@H:2]1[CH2:15][C@@H:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=3[C@@H:5]2[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24]>CC(C)=O>[OH:1][CH:2]1[CH2:15][CH:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:24][CH:23]=[CH2:22])=[CH:10][C:9]=3[CH:5]2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 15709503HCID 15709503, compound

Product 1

HCID 54309998HCID 54309998, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.40 g (6.86 mmol) of the product of Example 5, Step A, 2.5 g (mmol) of K2CO3 and 2.4 g (mmol) of allyl bromide in 10 mL of dry acetone was heated under reflux for 18 h. The solution was partitioned between ether and water and the aqueous layer was extracted with ether. The organic extractes were washed with saturated Na2CO3 solution and brine, and the combined extracts were dried over MgSO4 and concentrated to an oil. This crystallized from ethyl acetate-hexane to afford 1.03 g of white prisms that was a single C3-diastereomer (75% based on a 4:1 mixture of starting epimers).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe solution was partitioned between ether and water
  4. extractionthe aqueous layer was extracted with ether
  5. washThe organic extractes were washed with saturated Na2CO3 solution and brine
  6. dry with materialthe combined extracts were dried over MgSO4
  7. concentrationconcentrated to an oil
  8. customThis crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-334373609558409ab6169dcebc446e24
Source dataset
uspto-grants-1990_12
Patent number
US04978679

Reaction notes

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