Ethyl Acetate → HCID 9921365, compound

HRID 2374189Notes

Reaction equation

HRID 2374189 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].C([Mg]Br)C.[CH3:13][C:14]1([CH3:23])[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16](=[O:22])[CH2:15]1.C(OCC)(=O)C>C1COCC1>[CH3:20][C:18]1([CH3:21])[CH2:19][C:14]([CH3:23])([CH3:13])[CH2:15][C:16]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)([OH:22])[CH2:17]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 843993,3,5,5-TetramethylcyclohexanoneHCID 137268EthynylpyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 9921365HCID 9921365, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2-ethynylpyridine (1.0 g, 10 mmol) in THF at −78° C. was added a 1.0 M solution of ethyl magnesium bromide in THF (10 mL, 10 mmol). After stirring at reduced temperature for 30 minutes a solution of 3,3,5,5-tetramethyl-cyclohexanone (1.5 g, 10 mmol) in THF was added rapidly. The mixture was allowed to warm to ambient temperature over 16 hours, then partitioned between water and ethyl acetate. The organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The resultant product was purified by flash column chromatography on silica gel eluting with 1:1 hexane:ethyl acetate to afford 3,3,5,5-tetramethyl-1-(2-pyridinylethynyl)cyclohexanol (250 mg, 10% yield) as a white solid. M.p. 126-127° C. 1H NMR (DMSO-d6, 300 MHz) Δ8.57 (m, 1H), 7.64 (m, 1H), 7.39 (d, J=5 Hz, 1H), 7.22 (m, 1H), 1.91 (d, J=9 Hz, 2H), 1.71 (d, J=9 Hz, 2H), 1.26 (s, 2H), 1.14 (s, 6H), 1.09 (s, 6H).

Workup

  1. additionwas added rapidly
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant product was purified by flash column chromatography on silica gel eluting with 1:1 hexane

Sources & evidence

ORD record
ord-906ee36053284fda92dcbcf89dc4dbc5
Source dataset
uspto-grants-2008_12
Patent number
US07462619B2

Reaction notes

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