Dimethylformamide → HCID 58546655, compound

HRID 2194958Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.C([Li])CCC.CCCCCC.CN([CH:27]=[O:28])C.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:27]=[O:28]

Participants

Conditions

Temperature: -40 °C

Procedure

1.30 g of (2) (0.008 mol) was dissolved in freshly distilled THF 35 mL under argon atmosphere, and the solution was cooled to −40° C. n-butyllithium 1.6M-hexane solution 5.6 mL (0.0088 mol) was added dropwise while the temperature was kept at −40° C. The mixture was then stirred at −40° C. for 30 min, after which dry DMF 1.28 mL (0.016 mol) was added. The contents were allowed to warm up to room temperature and stirred overnight. Sodium bicarbonate solution was added, then THF was dried (Rotavap), extracted by CHCl3, dried over Na2SO4, and dried (Rotavap) until a light yellow oil was left. The product was purified by silica gel flash column chromatography, CHCl3:CH3OH=50:1. 0.861 g product (3) (57% yield) was obtained as a light yellow oil. As an alternative to column chromatography, the product (3) is purified by vacuum distillation.

Workup

additionwas added dropwise while the temperature
customwas kept at −40° C
temperatureto warm up to room temperature
stirringstirred overnight
dry with materialTHF was dried (Rotavap)
extractionextracted by CHCl3
dry with materialdried over Na2SO4
customdried (Rotavap) until a light yellow oil
waitwas left
customThe product was purified by silica gel flash column chromatography, CHCl3

Sources & evidence

ORD record: ord-284cfcc086d54dd28e14ba66aa45db18
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334377B2

Reaction notes

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