Methanol → 4-[(E)-3-(5-methoxy-furan-2-yl)-acryloyl]-benzamide

HRID 2362194Notes

Reaction equation

C[O-].[Na+].[C:4]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[O:12])=[CH:9][CH:8]=1)(=[O:6])[CH3:5].[CH3:16][O:17][C:18]1[O:22][C:21]([CH:23]=O)=[CH:20][CH:19]=1.CO>CN(C)C=O>[CH3:16][O:17][C:18]1[O:22][C:21](/[CH:23]=[CH:5]/[C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[O:12])=[CH:9][CH:8]=2)=[O:6])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Sodium methoxide (in portions) was added, over a time interval of about three minutes, to 4-acetyl-benzamide (1.38 g, 8.5 mmol) and 5-methoxy-furan-2-carbaldehyde (1.31 g, 10.6 mmol) in a 1:1 mixture of methanol and dimethylformamide (16 mL). The resulting solution was placed under N2 and stirred overnight at 45° C. The reaction mixture was then evaporated to dryness under vacuum, followed by the addition of water and brine (100 mL) to the resulting residue. The aqueous solution was extracted with ethyl acetate (125 mL×3) and the combined organic layers were washed with brine (100 mL) and dried over MgSO4. The crude reaction mixture of 4-[(E)-3-(5-methoxy-furan-2-yl)-acryloyl]-benzamide and unreacted 4-acetyl acetamide is used without purification.

Workup

customThe reaction mixture was then evaporated to dryness under vacuum
additionfollowed by the addition of water and brine (100 mL) to the resulting residue
extractionThe aqueous solution was extracted with ethyl acetate (125 mL×3)
washthe combined organic layers were washed with brine (100 mL)
dry with materialdried over MgSO4
customThe crude reaction mixture of 4-[(E)-3-(5-methoxy-furan-2-yl)-acryloyl]-benzamide and unreacted 4-acetyl acetamide
customis used without purification

Sources & evidence

ORD record: ord-1f816030681246f4ad5bc4ba5f7cd4e2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691816B2

Reaction notes

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