Water → 4-Hydroxy-4-(3-pyridyl)cyclohexanone ethylene acetal

HRID 655155Notes

Reaction equation

HRID 655155 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14]1.O>CCOCC.C1COCC1>[CH2:14]1[O:15][C:16]2([CH2:21][CH2:20][C:19]([OH:22])([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[CH2:18][CH2:17]2)[O:23][CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 122863-BromopyridineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 200349044-Hydroxy-4-(3-pyridyl)cyclohexanone ethylene acetalYield 47%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of n-BuLi (1.59 M in Hexane, 45 mL. 71.6 mmol) in dry ether (150 mL) was added a solution of 3-Bromopyridine (11.24 g, 71.1 mmol) in dry ether (70 mL) dropwise at −78° C. After stirring for 10 min, a solution of cyclohexane-1,4-dione monoetylene acetal (9.25 g, 59.2 mmol) in THF (70 mL) was added over a period of 20 min at −78° C., and stirred for 3 h. To the reaction mixture was added with water. The aqueous layer was extracted with CH2Cl2, and the organic layer was washed with brine. The extracts were combined with the organic layer. After drying and concentration, the crude product was purified by column chromatography (Hexane/EtOAc=2/1) to yield 4-hydroxy-4-(3-pyridyl)cyclohexanone ethylene acetal (6.55 g, 47%) as a pale yellow powder.

Workup

  1. stirringstirred for 3 h
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe organic layer was washed with brine
  4. customAfter drying
  5. concentrationconcentration
  6. customthe crude product was purified by column chromatography (Hexane/EtOAc=2/1)

Sources & evidence

ORD record
ord-59143799378743cc90b1758e20f099c1
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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