HCID 18783146, compound → HCID 18783147, compound

HRID 1420871Notes

Reaction equation

HRID 1420871 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([CH2:10][C:11](OCC)=[O:12])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:8][C:6]1([CH3:9])[CH2:7][C:2]([CH3:1])([CH3:16])[CH2:3][CH:4]([CH2:10][CH2:11][OH:12])[CH2:5]1

Participants

4

Reactant 2

HCID 18783146HCID 18783146, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18783147HCID 18783147, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3,3,5,5-tetramethylcyclohexylacetate 8 (1.8 g, 8.0 mmol) in ether (30 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (0.9 g, 24.0 mmol) in ether (30 ml), which was cooled in an ice bath. The reaction mixture was refluxed for 3 h, cooled and residual lithium aluminum hydride was destroyed with water. The aqueous layer was separated and twice extracted with ether. The combined ether phases were washed with saline, dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography on silica gel, eluting with hexane-ethyl acetate mixture (4:1) to give 1.2 g (79%) of 11 as an oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. temperatureThe reaction mixture was refluxed for 3 h
  3. temperaturecooled
  4. customresidual lithium aluminum hydride was destroyed with water
  5. customThe aqueous layer was separated
  6. extractiontwice extracted with ether
  7. washThe combined ether phases were washed with saline
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography on silica gel
  12. washeluting with hexane-ethyl acetate mixture (4:1)

Sources & evidence

ORD record
ord-938cd098ff1544f0a672dc89beceaa05
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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