HCID 66934326, compound → HCID 86651014, compound

HRID 2093299Notes

Reaction equation

HRID 2093299 reaction equation
[CH:1]([CH:4]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[CH2:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:13]([Mg]Br)#[CH:14]>C1COCC1>[C:13]([C:9]1([OH:10])[CH:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH2:7][C:8]1([CH3:12])[CH3:11])#[CH:14]

Participants

4

Reactant 2

HCID 66934326HCID 66934326, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 86651014HCID 86651014, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 6-isopropyl-2,2-dimethylcyclohexanone (12.6 g, 75.0 mmol) in THF (50 ml) was added within 10 min at room temperature to a stirred solution of ethynyl magnesium bromide in THF (0.5 M, 180 ml, 90 mmol), and the reaction mixture was stirred for 2 d at 60° C. The reaction mixture was allowed to cool to room temperature, quenched with satd. aq. NH4Cl solution (500 ml) and extracted with Et2O (3×300 ml). The combined organic extracts were dried (Na2SO4) and evaporated. Purification of the resulting residue by silica gel FC (pentane/Et2O, 98:2, Rf 0.21) furnished 1-ethynyl-6-isopropyl-2,2-dimethylcyclohexanol (11.8 g, 81%) as a colorless liquid.

Workup

  1. temperatureto cool to room temperature
  2. customquenched with satd
  3. extractionaq. NH4Cl solution (500 ml) and extracted with Et2O (3×300 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. customevaporated
  6. customPurification of the resulting residue by silica gel FC (pentane/Et2O, 98:2, Rf 0.21)

Sources & evidence

ORD record
ord-3a2c23a0d49a4398b6ace00769e61307
Source dataset
uspto-grants-2013_05
Patent number
US08445424B2

Reaction notes

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