Ethanol → 2-Hydroxymethyl-5-methylpyrazine-4-oxide

HRID 2286699

Reaction equation

[C:1]([C:4]1[CH:9]=[N+:8]([O-:10])[C:7]([CH3:11])=[CH:6][N:5]=1)(O)=[O:2].B#B.C(O)C.C([O-])([O-])=O.[K+].[K+]>COCCOCCOC.O1CCCC1>[OH:2][CH2:1][C:4]1[CH:9]=[N+:8]([O-:10])[C:7]([CH3:11])=[CH:6][N:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Method B--To a solution of 2-carboxy-5-methyl-pyrazine-4-oxide (1.5 g) in diethylene glycol dimethyl ether (80 ml) addition was made at 0° C. under an atmosphere of nitrogen of a solution (1 M) of diborane in tetrahydrofuran (30 ml). To the reaction mixture maintained for 3 hours at 0° C. and 1 hour at room temperature, cautious addition was made of ethanol (50 ml) and then of a 0.5 M solution of alcoholic potash (25 ml). The resultant solution after evaporation at reduced pressure was taken up with chloroform which, on evaporation to dryness, gave 1.2 g of 2-hydroxymethyl-5-methyl-pyrazine-4-oxide.

Workup

additioncautious addition
customThe resultant solution after evaporation at reduced pressure
customwas taken up with chloroform which, on evaporation to dryness

Sources & evidence

ORD record: ord-97dcf43bbb0f44b29e1906d04cb7bd67
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04267327

Linked notes

Loading…