Dimethylformamide → 2-Chloro-5-(methoxymethoxy)isonicotinaldehyde

HRID 2044237Notes

Reaction equation

C([Li])(C)(C)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH3:16])=[CH:9][N:8]=1.CN(C)[CH:19]=[O:20].[NH4+].[Cl-]>CCCCC.C(OCC)C>[Cl:6][C:7]1[CH:12]=[C:11]([C:10]([O:13][CH2:14][O:15][CH3:16])=[CH:9][N:8]=1)[CH:19]=[O:20]

Participants

Conditions

Temperature: -76 °C

Procedure

tert-Butyllithium in pentane (1.7 M, 19.0 mL) was added dropwise to a solution of 2-chloro-5-(methoxymethoxy)pyridine (4.880 g, 28.11 mmol) in 100 ml of ethyl ether at −76° C. Some precipitate appeared. The mixture was kept at −76° C. for 20 min then N,N-dimethylformamide (2.938 mL, 37.95 mmol) was added dropwise. The mixture was stirred for 10 min at −76° C. and then allowed to warm to at 0° C. for 1 h period. 10% aq NH4Cl was added and the mixture was extracted with ethyl acetate. The organic solution was washed with water, brine and dried over Na2SO4. After concentration in vacuum the yield of the crude 2-chloro-5-(methoxymethoxy)isonicotinaldehyde 5.49 g. MS: 202.0, 172.0. Without further purification was used in the next step.

Workup

temperatureto warm to at 0° C. for 1 h period
extractionthe mixture was extracted with ethyl acetate
washThe organic solution was washed with water, brine
dry with materialdried over Na2SO4
concentrationAfter concentration in vacuum the yield of the crude 2-chloro-5-(methoxymethoxy)isonicotinaldehyde 5.49 g
customWithout further purification

Sources & evidence

ORD record: ord-4048d89f5b23438c91956c3ed7af1456
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586574B2

Reaction notes

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