Ethanol → 1262803-60-0

HRID 2195763Notes

Reaction equation

HRID 2195763 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[O-:12][CH2:13][CH3:14].[Na+].O.[CH2:17](O)C>>[CH2:13]([O:12][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:17])=[O:9])=[N:6][CH:7]=1)[CH3:14]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 668696851262803-60-0

Procedure

A stirred solution of methyl 5-chloropyrazine-2-carboxylate (0.50 g) in ethanol (10 mL) was cooled to 0° C., and sodium ethoxide (21% w/w solution in ethanol, 1 mL) was added over 10 mins. After allowing to warm to RT and stir for 2 h, water (100 mL) was added and the mixture extracted with EtOAc (2×150 mL). The combined organic portions were dried over MgSO4 and evaporated to afford the title compound. (0.65 g, purity approx. 85%). 1H NMR (400 MHz, CDCl3) δ ppm 1.45 (t, J=7.1 Hz, 3 H), 1.46 (t, J=7.1 Hz, 3H), 4.48 (q, J=7.1 Hz, 2H), 4.49 (q, J=7.1 Hz, 2H), 8.28 (d, J=1.3 Hz, 1H), 8.88 (d, J=1.3 Hz, 1H)

Workup

  1. extractionthe mixture extracted with EtOAc (2×150 mL)
  2. dry with materialThe combined organic portions were dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-45f6b16f2775492385328587fc92097d
Source dataset
uspto-grants-2012_12
Patent number
US08338407B2

Reaction notes

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