Diethyl Ether → HCID 22630121, compound

HRID 2307088Notes

Reaction equation

HRID 2307088 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[CH:10]C(OCC)=O)[CH2:3]1.[Li][CH3:18].[NH4+].[Cl-].C([O:23][CH2:24][CH3:25])C>>[CH3:18][C:24]([OH:23])([CH3:25])[CH:10]=[C:4]1[CH2:3][C:2]([CH3:16])([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5]1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 15307456Ethyl (3,3,5,5-tetramethylcyclohexylidene)acetateHCID 178418348HCID 178418348, compound

Product 1

HCID 22630121HCID 22630121, compoundYield 86%

Procedure

A solution of acetate 2 (2.14 g, 10 mmol) in diethyl ether (20 ml) was added to 1.6 M MeLi solution in diethyl ether (26 ml, 40 mmol), while cooling in an ice bath. The reaction mixture was stirred at room temperature for 1 h. It was then cooled in an ice bath and saturated aqueous NH4Cl (20 ml) was added dropwise. The aqueous phase was extracted with diethyl ether (230 ml). The combined organic phases were washed with brine (30 ml), dried over MgSO4, filtered and evaporated. The residue was purified by Kugelrohr short path distillation (100° C./4 mm Hg) to give 29 (1.86 g, 86%) as a colorless oil. 1H-NMR: (CDCl3, TMS): 0.91 and 0.96 (total 12H, both s, c-Hex-3,5-CH3); 1.25 (2H, s, c-Hex-4-CH2); 1.38 (6H, s, —C(CH3)2O); 1.79 and 2.23 (both 2H, both s, c-Hex-2,6-CH2) and 5.39 ppm (1H, s, ═CH—).

Workup

  1. temperaturewhile cooling in an ice bath
  2. temperatureIt was then cooled in an ice bath
  3. extractionThe aqueous phase was extracted with diethyl ether (230 ml)
  4. washThe combined organic phases were washed with brine (30 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue was purified by Kugelrohr short path distillation (100° C./4 mm Hg)

Sources & evidence

ORD record
ord-a14f3fd6748d4e5e8ae96509e54c8152
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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