Reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=O)[CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Si](OCC)(OCC)(OCC)OCC.[CH:26]([C:29]1[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]([CH3:38])[CH3:37])[C:30]=1[NH2:31])([CH3:28])[CH3:27].OS(O)(=O)=O>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](/[C:9](=[N:31]/[C:30]2[C:32]([CH:36]([CH3:37])[CH3:38])=[CH:33][CH:34]=[CH:35][C:29]=2[CH:26]([CH3:28])[CH3:27])/[CH3:10])[C:3]=1[OH:12]Participants
Conditions
- Temperature
- 170 °C
Procedure
In a 50 mL Claisens flask under argon atmosphere, a mixture of 10.6 g (46.3 mmol) of 29, 20.2 g (97.2 mmol) of Si(OEt)4, and 9.03 g (50.9 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.37 mL of 96% H2SO4 was added. This mixture was stirred for 5 hr, and the formed ethanol was slowly distilled off. Later, 300 mL of cold water was added, and the product was extracted with 2×100 mL of diethyl ether. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: hexanes and then hexanes-diethyl ether, 100:1, vol.). The isolated product was additionally washed with 3×30 mL hexanes and dried in vacuum. This procedure gave 14.7 g (82%) of yellowish solid.
Workup
- distillationthe formed ethanol was slowly distilled off
- additionLater, 300 mL of cold water was added
- extractionthe product was extracted with 2×100 mL of diethyl ether
- extractionThe combined extract
- dry with materialwas dried over K2CO3
- customevaporated to dryness
- customThe product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent
- washThe isolated product was additionally washed with 3×30 mL hexanes
- customdried in vacuum
Sources & evidence
- ORD record
- ord-44bb10bde4aa4d528f643a0d864ea08d
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541521B2
Linked notes
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