Diethyl Ether → HCID 18783152, compound

HRID 1636458Notes

Reaction equation

HRID 1636458 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([CH2:10]C(OCC)=O)[CH2:3]1.[CH3:17][Mg]I.CC[O:22][CH2:23][CH3:24]>>[CH3:17][C:23]([OH:22])([CH3:24])[CH2:10][CH:4]1[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2]([CH3:16])([CH3:1])[CH2:3]1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 18783146HCID 18783146, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 18783152HCID 18783152, compoundYield 80%

Procedure

A solution of ethyl 3,3,5,5-tetramethylcyclohexylacetate (8) (2.26 g, 10 mmol) in ether (20 ml) was added dropwise to a 2 M methylmagnesium iodide solution in ether (20 ml) over 15 min, while cooling with ice water. The mixture was refluxed for 2 h, cooled and quenched with saturated aqueous NH4Cl. After traditional workup the product was purified on silica gel column, eluting with a mixture of hexane-ethyl acetate (20:1) to give 1.7 g (80%) of 9 as an oil.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperaturecooled
  3. customquenched with saturated aqueous NH4Cl
  4. customAfter traditional workup the product was purified on silica gel column
  5. washeluting with a mixture of hexane-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-058d7ecc2f5b43a3a768854af892341b
Source dataset
uspto-grants-2000_03
Patent number
US06034134

Reaction notes

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