Cyclohexanone → HCID 10352983, compound

HRID 2248452Notes

Reaction equation

HRID 2248452 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=1.[C:15]1(=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CCCCC>C(OCC)C>[OH:21][C:15]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 8003PentaneHCID 27348955-Bromo-2-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 10352983HCID 10352983, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of n-butyllithium (1.6M in hexanes, 150 ml) was added dropwise over 1 hour to a mechanically stirred solution of 5-bromo-2-methoxypyridine (39.3 g) in 800 ml of diethyl ether at -40° C. The resulting slurry was stirred at -40° C. to -45° C. for 45 minutes, and then cyclohexanone (23.5 g) in 50 ml of diethyl ether was added dropwise over 1 hour. The mixture was allowed to warm to 0° C. over about 1 hour, and then the reaction was quenched with saturated ammonium chloride solution. The layers were separated, and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to yield a semi-solid material. Trituration with pentane provided 29.0 g of product as a powder. Recrystallization of 8 g of the product gave 6.2 g of plates, m.p. 74°-75° C.

Workup

  1. customthe reaction was quenched with saturated ammonium chloride solution
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. washThe combined organic phases were washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a semi-solid material

Sources & evidence

ORD record
ord-1b2360c12b6f4133971d74dc3c2a3141
Source dataset
uspto-grants-1991_08
Patent number
US05039809

Reaction notes

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