Diethyl Ether → Methyl 3,6-dimethylpicolinate

HRID 1958314Notes

Reaction equation

HRID 1958314 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.CCOCC.[CH3:13][C:14]1[C:15]([C:21]([OH:23])=[O:22])=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1>C1C=CC=CC=1.CO.C(OCC)(=O)C>[CH3:1][O:22][C:21]([C:15]1[C:14]([CH3:13])=[CH:19][CH:18]=[C:17]([CH3:20])[N:16]=1)=[O:23]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 132095673,6-Dimethylpyridine-2-carboxylic acid

Product 1

HCID 10511234Methyl 3,6-dimethylpicolinateYield 53.2%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trimethylsilyldiazomethane 2M in ether (5.7 ml, 11.4 mmole, 1.4 eq.) is added dropwise at RT to a suspension of 3,6-dimethyl-pyridine-2-carboxylic acid (containing potassium chloride) (3.07 g à 25%, 8.12 mmole, 1 eq.) in benzene (24 ml) and methanol (8 ml), and the yellow suspension is stirred at RT for 1.5 h. The yellow mixture is diluted with ethyl actate, washed once with sat. aqueous sodium bicarbonate sol., once with water, once with brine, dried with magnesium sulfate and the solvents are removed in vacuo. Purification of the residue (914 mg) by chromatography on a 20 g Silicycle silica cartridge (eluent heptane/ethyl acetate 5-40% 20 min) affords 3,6-dimethyl-pyridine-2-carboxylic acid methyl ester (714 mg, 53.2%) as a colorless liquid. MS (m/e)=166.3 [M+H+].

Workup

  1. washwashed once with sat. aqueous sodium bicarbonate sol., once with water, once with brine
  2. dry with materialdried with magnesium sulfate
  3. customthe solvents are removed in vacuo
  4. customPurification of the residue (914 mg) by chromatography on a 20 g Silicycle silica cartridge (eluent heptane/ethyl acetate 5-40% 20 min)

Sources & evidence

ORD record
ord-324141fa136d4393bb1d3f5fe02b72a9
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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