Acetone → HCID 13866078, compound

HRID 2226004Notes

Reaction equation

HRID 2226004 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 (1.5 M 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 2.5 N 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) d 2.20 (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-72e5514f4cf3485482f5b57d793ffe3f
Source dataset
uspto-grants-1994_09
Patent number
US05344991

Reaction notes

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