Tetrahydrofuran → (2E)-3-[4-(tert-Butyl)phenyl]-N-[3-(2-hydroxyethoxy)phenyl]prop-2-enamide

HRID 730260Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C[O:26][CH2:25][CH2:24]1.BrCCO>[OH-].[Na+]>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:24][CH2:25][OH:26])[CH:17]=2)=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a round-bottomed flask, equipped with magnetic stirring and reflux condenser, was added (2E)-3-[4-(tert-butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide, Example 23, (200 mg, 0.68 mmol), THF (10 mL), 2-bromoethanol (200 uL, 2.80 mmol, Aldrich) and 5 N NaOH (10 mL). The reaction mixture was stirred at reflux for 5 h. After allowing to cool to 25° C., the mixture was extracted with EtOAc (20 mL). The organic extract was washed with water (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (2:1 hexane:EtOAc) provided the title product as a colorless oil. MS (ESI, pos. ion) m/z: 340 (M+1).

Workup

customTo a round-bottomed flask, equipped
temperaturereflux condenser
stirringThe reaction mixture was stirred
temperatureat reflux for 5 h
extractionthe mixture was extracted with EtOAc (20 mL)
extractionThe organic extract
washwas washed with water (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by silica gel chromatography (2:1 hexane:EtOAc)

Sources & evidence

ORD record: ord-d573b4fff0824ce0958097b755df3969
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582657B2

Reaction notes

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