Methanol → Methyl pyrazinoate

반응식

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:15]O>>[CH3:15][O:8][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9]

참가 물질

반응물 3

HCID 887Methanol

HCID 10472-Pyrazinecarboxylic acid

HCID 1118Sulfuric Acid

생성물 1

HCID 72662Methyl pyrazinoate수율 59%

실험 절차

A solution of 2-pyrazinecarboxylic acid (2.00 g, 16.1 mmol) and H2SO4 (catalytic) in MeOH (50 mL) was heated at reflux for 45 minutes, then concentrated in vacuo. The residue was partitioned between EtOAc (40 mL) and saturated NaHCO3(aq) (20 mL). The organic phase was washed with saturated NaHCO3(aq) (20 mL) and brine (10 mL), then dried (MgSO4) and concentrated in vacuo to give colourless crystals (1.32 g, 59%). 1H NMR (CDCl3) □ 4.04 (s, 3H), 8.72 (dd, 11H, J=2.4, 1.2 Hz), 8.77 (d, 1H, J=2.4 Hz), 9.32 (d, 1H, J=1.2 Hz).

후처리

temperatureat reflux for 45 minutes
concentrationconcentrated in vacuo
customThe residue was partitioned between EtOAc (40 mL) and saturated NaHCO3(aq) (20 mL)
washThe organic phase was washed with saturated NaHCO3(aq) (20 mL) and brine (10 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

출처 및 근거

ORD 기록: ord-1245e15db51147829497f5c1ab0ba500
출처 데이터셋: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07084155B2

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