HCID 18783146, compound → HCID 18783147, compound

HRID 1636459Notes

Reaction equation

HRID 1636459 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 hydnde 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. 1H NMR (CDCl3, TMS) δ: 0.89 and 1.00 (total 12H, both s, cyclohexane 3,5-CH3); 1.44 (2H, q, J=7 Hz, 2-CH2); 0.55-1.95 (8H, m, ring protons and OH) and 3.70 ppm (2H, t, J=7 Hz, CH2O).

Workup

  1. temperaturewas cooled in an ice bath
  2. temperatureThe reaction mixture was refluxed for 3 h
  3. temperaturecooled
  4. customresidual lithium aluminum hydnde 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

Sources & evidence

ORD record
ord-b336f6266a1b45a9ac36c71872c82a2a
Source dataset
uspto-grants-2000_03
Patent number
US06034134

Reaction notes

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