Diethyl Ether → Cyclohexanol, 1-ethynyl-, 1-acetate

HRID 270441

Reaction equation

HRID 270441 reaction equation
[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[C:10](OC(=O)C)(=[O:12])[CH3:11].C([O-])(O)=O.[Na+].CCOCC>C(#N)C.C1COCC1.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[C:10]([O:9][C:3]1([C:1]#[CH:2])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)(=[O:12])[CH3:11]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 65251-EthynylcyclohexanolHCID 7918Acetic AnhydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 78903Cyclohexanol, 1-ethynyl-, 1-acetateYield 110.7%

Reagents, catalysts & solvents 3

HCID 2734571Scandium(III) triflateCatalyst2×HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 3.1 g (25 mmol) 1-ethynyl-1-cyclohexanol in 25 ml acetonitrile were added 7.1 ml (75 mmol, 3 eq) acetic anhydride at −20° C. 12.3 mg (0.03 mmol) scandiumtriflate in 300 μl THF were added and the solution was stirred for 2 h. Additional 12.3 mg (0.03 mmol) scandiumtriflate in 300 μl THF were added and stirring was continued for 30 min. A saturated aqueous solution of NaHCO3 and ether were added. The layers were separated and the inorganic one was extracted with ether. The combined organic phases were washed with brine and dried over Na2SO4. Evaporation yielded 4.6 g crude 1-ethynylcyclohexyl acetate as colorless oil, MS: 166 (M).

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. customThe layers were separated
  4. extractionthe inorganic one was extracted with ether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation

Sources & evidence

ORD record
ord-a67f1e0cc08c4f6a98f30aa3663cf99f
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Linked notes

Loading…