Acetone → HCID 21541491, compound

HRID 1076014Notes

Reaction equation

HRID 1076014 reaction equation
[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[C:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]1[CH:33]([C:34]#[N:35])[CH:32]([OH:36])[CH2:31][C:30]1=[O:37])([O:21][CH3:22])=[O:20].CC(C)=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O1CCCC1>[C:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]1[CH:33]([C:34]#[N:35])[CH:32]([OH:36])[CH2:31][CH:30]1[OH:37])([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6097028Ammonium SulfateHCID 16710494Lithium tri-tert-butoxyaluminohydride2×HCID 21541490HCID 21541490, compound

Product 1

HCID 21541491HCID 21541491, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a suspension of 8 g of lithium tri-t-butoxyaluminum hydride in 90 ml of absolute tetrahydrofuran was added dropwise 4.0 g of 2-(6'-carbomethoxyhexyl)-3-cyano-4-hydroxy-cyclopentanone under ice-cooling. The obtained mixture remained under ice-cooling for 1.5 hours and then at room temperature for 0.5 hours. After cooling, acetone and an aqueous solution saturated with ammonium sulfate were added to the reaction mixture to decompose the excess lithium tri-t-butoxyaluminum hydride and the complex salt product. The resultant oily layer was extracted with ethyl acetate, and the extract was washed with water, dried and then concentrated to afford 3.2 g of 2-(6'-carbomethoxyhexyl)-3-cyano-cyclopentane-1,4-diol as an oily substance, which was purified using chromatography on silica gel.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1.5 hours
  3. temperatureAfter cooling
  4. extractionThe resultant oily layer was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b41e421a838a41028fb6c32d88c6dbe5
Source dataset
uspto-grants-1976_05
Patent number
US03954811

Reaction notes

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