1,8-Diazabicyclo(5.4.0)undec-7-ene → (2-Chloro-4-cyano-5-methoxyphenyl)ethylene

HRID 1474255Notes

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([C:16]#[N:17])=[CH:10][C:9]=1[Cl:18])(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:18][C:9]1[CH:10]=[C:11]([C:16]#[N:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=1[CH:7]=[CH2:6]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 2-(2-chloro-4-cyano-5-methoxyphenyl)ethyl methanesulfonate (274 mg, 0.945 mmol) in DCM (4 mL) was treated with DBU (0.712 mL, 4.73 mmol) and stirred for 3 hours at 50° C., then at RT for 12 hours. TLC (50% ethyl acetate/hexanes) showed complete conversion to a faster intense UV band for the product. The reaction was then diluted with DCM and aq. citric acid and the mixture was extracted twice with DCM. The organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography (10-20% ethyl acetate/hexanes) afforded the title intermediate.

Workup

waitat RT for 12 hours
extractionthe mixture was extracted twice with DCM
washThe organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customPurification of the residue by flash chromatography (10-20% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-0db34990965245b693f70fe50f28291b
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018211B2

Reaction notes

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