Acetonitrile → HCID 67496220, compound

HRID 1628346Notes

Reaction equation

[C:1](#[N:3])[CH3:2].C([Li])CCC.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][N:20]=1)[C:14](OC)=[O:15]>C1COCC1>[C:1]([CH2:2][C:14]([C:13]1[CH:18]=[CH:19][N:20]=[C:11]([O:10][CH3:9])[CH:12]=1)=[O:15])#[N:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a 100 ml flask was added 30 ml of THF and acetonitrile (1.41 ml, 26.9 mmole). The mixture was cooled to −78° C. and then n-butyllithium (16.8 ml, 26.9 mmole, 1.6M solution in hexane) was added. The reaction was stirred for 30 minutes at which time 5 ml of a THF solution of methyl 2-methoxyisonicotinate 105.1.A (1.50 g, 9.0 mmole) was added. After 3 hours at −78° C., the reaction mixture was quenched by 1.7 ml of acetic acid, and was warmed to room temperature. The solvent was removed by rotary evaporation and the crude was purified on a silica gel column to give 105.1.B (676 mg, 43% yield) as orange crystals.

Workup

additionwas added
customthe reaction mixture was quenched by 1.7 ml of acetic acid
temperaturewas warmed to room temperature
customThe solvent was removed by rotary evaporation
customthe crude was purified on a silica gel column

Sources & evidence

ORD record: ord-4942a123e253406c9a242a8200002536
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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