Ethanol → Ethyl 2-(3-chloropyrazin-2-yl)acetate

HRID 1852894Notes

Reaction equation

HRID 1852894 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][C:9]([OH:11])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1.C(N1C=CN=C1)(N1[CH:18]=[CH:17]N=C1)=O.C(O)C>CN(C)C=O>[CH2:17]([O:10][C:9](=[O:11])[CH2:8][C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=1)[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 71748594(3-Chloropyrazin-2-yl)acetic acid

Product 1

HCID 53419385Ethyl 2-(3-chloropyrazin-2-yl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-chloro-pyrazin-2-yl)-acetic acid (2.00 g) in N,N-dimethylformamide (“DMF”) (20 ml) was added 1,1′-carbonyldiimidazole (1.88 g) and the mixture stirred for 1 hour. To the reaction mixture was added ethanol (20 ml) and the mixture stirred for 1 hour at ambient temperature. The reaction mixture was concentrated and then purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane) to give (3-chloro-pyrazin-2-yl)-acetic acid ethyl ester (1.93 g). 1H-NMR (400 MHz, CDCl3): 8.50 (s, 1H), 8.30 (s, 1H), 4.20 (q, 2H), 4.00 (s, 2H), 1.30 (t, 3H) ppm.

Workup

  1. stirringthe mixture stirred for 1 hour at ambient temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-dfb530c6e9fe4d288c1dd9f9e52a3314
Source dataset
uspto-grants-2015_02
Patent number
US08962628B2

Reaction notes

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