Diethyl Ether → HCID 67415336, compound

HRID 912708Notes

Reaction equation

HRID 912708 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:9][CH3:10])[CH:6]([OH:8])[CH3:7].Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl.C(OCC)C>CN(C=O)C.[Cl-].[Na+].O.O>[CH3:3][O:4][CH:5]([O:9][CH3:10])[CH:6]([CH3:7])[O:8][CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 5543781,1-Dimethoxy-2-propanol

Product 1

HCID 67415336HCID 67415336, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (1.80 g, 45.0 mmol, 60% dispersion in mineral oil) was added slowly to a solution of 1,1-dimethoxypropan-2-ol (2.16 g, 18.0 mmol) (Prepared according to the method described by Hunter et al. Tetrahedron, 1994, 50, 871-888.) in DMF (25 mL) immersed in an ice bath. After the addition was complete, the ice bath was removed to allow the solution to warm to r.t. Then the reaction flask was placed in an ice bath and 2-picolylchloride hydrochloride (2.95 g, 18.0 mmol) was slowly added. After warming to r.t. overnight, diethyl ether, water and brine were added. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by silica gel column chromatography (hexanes/ethyl acetate, first 4:1 then 1:1) resulting in the isolation of 1.74 g (46% yield, 8.22 mmol) of the title compound.

Workup

  1. customPrepared
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. customThen the reaction flask was placed in an ice bath
  5. temperatureAfter warming to r.t. overnight
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with diethyl ether
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe product was purified by silica gel column chromatography (hexanes/ethyl acetate, first 4:1

Sources & evidence

ORD record
ord-24a781305171492b9129923f17c9c141
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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