Dimethyl Carbonate → Methyl 2-(6-methoxypyridin-2-yl)acetate

HRID 572913Notes

Reaction equation

HRID 572913 reaction equation
[Li+].CC([N-]C(C)C)C.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1.[C:18](=O)([O:21]C)[O:19][CH3:20]>C1COCC1>[CH3:9][O:10][C:11]1[N:12]=[C:13]([CH2:17][C:18]([O:19][CH3:20])=[O:21])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 2724682Lithium diisopropylamideHCID 53247732-Methoxy-6-methylpyridine

Product 1

HCID 86719093Methyl 2-(6-methoxypyridin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of LDA (18.3 mL, 36.5 mmol) in THF (120 mL) cooled to −78° C. was added 2-methoxy-6-methylpyridine (1.5 g, 12.2 mmol) in THF (15 mL) dropwise, and then the mixture was stirred at −78 degree for 2 h. Dimethyl carbonate (1.2 mL, 14.6 mmol) was added quickly and continued to stir at −78° C. for 15 min. The reaction was quenched by H2O at −78° C. The solution was extracted with ethyl acetate, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified with a standard method to give desired compound.

Workup

  1. stirringto stir at −78° C. for 15 min
  2. customThe reaction was quenched by H2O at −78° C
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified with a standard method

Sources & evidence

ORD record
ord-4d14ca8d2b144a41b5c2a8fa87c5c1be
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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