1-Ethynylcyclohexanol → HCID 58399442, compound

HRID 888272Notes

Reaction equation

HRID 888272 reaction equation
[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].C([Li])CCC.[C:15]1([CH3:23])[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1>O1CCCC1>[OH:22][CH:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:23])=[CH:16][CH:17]=1)[C:2]#[C:1][C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 65251-EthynylcyclohexanolHCID 77254-MethylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 58399442HCID 58399442, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-ethynylcyclohexanol (500 mg, 4.02 mmol) in tetrahydrofuran (20 mL), 2.77 M n-butyllithium (solution in n-hexane, 3.6 mL, 9.90 mmol) was added dropwise at −78° C., and the obtained solution was stirred at the same temperature for 1 hour. To the reaction solution, p-tolualdehyde (0.52 mL, 4.40 mmol) was added at −78° C., and the obtained solution was allowed to warm gradually to room temperature with stirring. To the reaction solution, distilled water and 1 M hydrochloric acid were added to make the mixture acidic, and the resultant was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (598 mg, 2.44 mmol, 61%) as a pale yellow solid.

Workup

  1. stirringwith stirring
  2. distillationTo the reaction solution, distilled water and 1 M hydrochloric acid
  3. additionwere added
  4. extractionthe resultant was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-abb15a84d94045f5bb8c828b7cebbb3b
Source dataset
uspto-grants-2012_08
Patent number
US08247569B2

Reaction notes

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