6-Methyl-2-pyridinecarboxaldehyde → 2-(1,3,-Dioxolan-2-yl)-6-methylpyridine

HRID 1258579Notes

Reaction equation

HRID 1258579 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=[CH:15][CH:16]=1.[OH2:21]>C(O)CO>[O:9]1[CH2:16][CH2:15][O:21][CH:8]1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 27343042-(1,3,-Dioxolan-2-yl)-6-methylpyridineYield 73.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 6-methylpyridine-2-carbaldehyde (3.7 g, 30.54 mmol, 1 eq.) in 10 ml of ethylene glycol was added TsOH.H2O (6.67 g, 32.07 mmol, 1.05 eq.). The reaction was heated in microwave at 200° C. for 180 s (fixed hold absorb high). The mixture was added to a stirred solution of 10 g of K2CO3 in 200 ml of water, and was extracted with DCM (3×150 ml). The combined organics were washed with water evaporated on RFE (water bath 25° C.) to give 2-(1,3-dioxolan-2-yl)-6-methylpyridine (3.7 g, 51% yield) as pale brown liquid.

Workup

  1. custom(fixed hold absorb high)
  2. additionThe mixture was added to a stirred solution of 10 g of K2CO3 in 200 ml of water
  3. extractionwas extracted with DCM (3×150 ml)
  4. washThe combined organics were washed with water
  5. customevaporated on RFE (water bath 25° C.)

Sources & evidence

ORD record
ord-0335bdbc9efd4eb08f4c3987307fc13e
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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