Diethyl Carbonate → Ethyl 2-(6-chloro-3-methylpyridin-2-YL)acetate

HRID 2235972Notes

Reaction equation

HRID 2235972 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[N:7]=1)[CH3:2].Cl[C:15]1N=C(C)C(C)=CC=1.[Li+].CC([N-]C(C)C)C.C(=O)(OCC)OCC>C1COCC1>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:11]([CH3:15])=[CH:10][CH:9]=[C:8]([Cl:12])[N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7766Diethyl CarbonateHCID 2724682Lithium diisopropylamideHCID 125083766-Chloro-2,3-dimethylpyridineHCID 18928624Ethyl 2-(6-chloropyridin-2-yl)acetate

Product 1

HCID 59300476Ethyl 2-(6-chloro-3-methylpyridin-2-YL)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure described for the preparation of ethyl(6-chloro-2-pyridinyl)acetate (Example 469) and starting from 6-chloro-2,3dimethylpyridine (0.35 g, 2.5 mmol), LDA (5.17 mmol), and diethyl carbonate (0.75 mL, 6.2 mmol) in THF (10 mL), the title compound was obtained (0.15 g, 29%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.42 (d, 1H), 7.15 (d, 1H), 4.18 (q, 2H), 3.84 (s, 2H), 2.29 (s, 3H), 1.27 (t, 3H); LC-MS: RT=2.30 min, (M+H)+ 214.2.

Sources & evidence

ORD record
ord-1067de62360c456c87fdceb3eaf29834
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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