Dimethylformamide → 2,6-Dichloro-4-morpholin-4-YL-benzaldehyde

HRID 1514949Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Li]C(CC)C.CN([CH:23]=[O:24])C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[C:7]=1[CH:23]=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of to a solution of 4-(3,5-dichlorophenyl)-morpholine (1.60 g, 6.93 mmol) in dry THF (20 mL) under N2 at −78° C. was added dropwise sec-BuLi (1.4M in cyclohexane, 5.44 mL). The solution was allow to stir for 30 min then DMF (2.68 mL, 34.7 mmol) was slowly added to the. Upon disappearance of the starting material by TLC, the reaction was warmed to 0° C. then was quench by addition of H2O (15 mL). The mixture was extracted with EtOAc (150 mL), the organic phase was dried over Na2SO4 and the solvent was evaporate under reduced pressure. The resulting solid was triturated with Et2O to yield 2,6-dichloro-4-morpholin-4-yl-benzaldehyde as an off white solid. 1H NMR (400 MHz, Acetonitrile-d3): δ 10.44 (s, 1H), 7.06 (s, 2H), 3.85-3.93 (m, 4H), 3.46-3.54 (m, 4H). MS (m/z) 260.0 (M+1).

Workup

customthen was quench by addition of H2O (15 mL)
extractionThe mixture was extracted with EtOAc (150 mL)
dry with materialthe organic phase was dried over Na2SO4
customthe solvent was evaporate under reduced pressure
customThe resulting solid was triturated with Et2O

Sources & evidence

ORD record: ord-6881c0f6e7c147ac92d4af0496a28c86
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

Loading…