Acetone → HCID 13866078, compound

HRID 1901101Notes

Reaction equation

HRID 1901101 reaction equation
[Br:1][C:2]1[CH2:6][C:5]([C:12](OCC)=[O:13])([C:7](OCC)=[O:8])[CH2:4][C:3]=1[Br:17].[H-].C([Al+]CC(C)C)C(C)C.CC(C)=O.[OH-].[Na+]>C1COCC1.O>[Br:1][C:2]1[CH2:6][C:5]([CH2:7][OH:8])([CH2:12][OH:13])[CH2:4][C:3]=1[Br:17]

Participants

7

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 138660771,2,-Dibromo-4,4-di(carboethoxy)cyclopenteneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13866078HCID 13866078, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, a stirred solution of 8.7 g (23.5 mmol) of 1,2-dibromo-4,4-di(carboethoxy)cyclopentene (Step 4) in 70 mL of anhydrous THF at -78° C. was treated with 80 mL of diisobutylaluminum hydride (1.5M in toluene) over a 20 minute period. The reaction was allowed to warm to ambient temperature overnight and was slowly treated with 20 mL of acetone followed by 10 mL of 2.5N sodium hydroxide. Water (100 mL) was added and the solution extracted 5 times with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo to give 5.7 g (85%) of 1,2-dibromo-4,4-di(hydroxymethyl)cyclopentene (10 in Synthetic Scheme III) as a colorless oil: NMR (CDCl3) δ2.20 (s, 2H), 2.50 (s, 4H), 3.70 (s, 4H).

Workup

  1. extractionthe solution extracted 5 times with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c848ebae074d419aa5444db2bf9c900b
Source dataset
uspto-grants-1996_11
Patent number
US05576339

Reaction notes

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