Dimethyl Sulfate → 2-((3-Ethoxy-4-methoxyphenyl)(methoxy)methylene)malononitrile

HRID 731896Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([OH:18])=[C:13]([C:16]#[N:17])[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[C:19](=O)(O)[O-].[Na+].O1CCOCC1.COS(OC)(=O)=O>O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([O:18][CH3:19])=[C:13]([C:14]#[N:15])[C:16]#[N:17])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

2-((3-ethoxy-4-methoxyphenyl)(hydroxy)methylene)malononitrile (25.5 mmol) and sodium bicarbonate (17 g, 204 mmol) were combined in a solution of 1,4-dioxane (48 mL) and water (8 mL). Dimethylsulphate (17 mL, 178 mmol) was slowly added and the reaction was heated to 80-90° C. for 2 hours. The reaction was cooled to RT, water was added, and the aqueous phase extracted three times with EtOAc (200 mL). The organic phases were combined, dried with MgSO4, and filtered to give a red oil. The oil was purified by silica gel chromatography (10% EtOAc/Hexanes, Rf˜0.1) to give a white solid (3.59 g, 54.5% yield over three steps). ESI-MS (M+H)+ m/z calcd 259.1, found 259.0.

Workup

temperatureThe reaction was cooled to RT
extractionthe aqueous phase extracted three times with EtOAc (200 mL)
dry with materialdried with MgSO4
filtrationfiltered
customto give a red oil
customThe oil was purified by silica gel chromatography (10% EtOAc/Hexanes, Rf˜0.1)
customto give a white solid (3.59 g, 54.5% yield over three steps)

Sources & evidence

ORD record: ord-8b075ac1779147a4a728a98418f1ce64
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585868B2

Reaction notes

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