3-(1-Adamantyl)-4-methoxyphenylacetylene → ethyl 2-[3-(1-Adamantyl)-4-methoxyphenylethynyl]-4-thiophenecarboxylate
Reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]#[CH:20])[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[C:22]1[S:23][CH:24]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:26]=1>>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]#[C:20][C:22]4[S:23][CH:24]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:26]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2Participants
3
Procedure
In a manner analogous to Example 1(b) above, by reaction of 3.2 g (12 mmol) of 3-(1-adamantyl)-4-methoxyphenylacetylene with 2.8 g (12 mmol) of ethyl 2-bromo-4-thiophenecarboxylate, there were obtained, after chromatography on a silica column eluted with a mixture of hexane and ethyl acetate, 2.4 g (48%) of the expected ethyl ester with the melting point 88°-90° C.
Workup
- customthere were obtained
- washafter chromatography on a silica column eluted with a mixture of hexane and ethyl acetate, 2.4 g (48%) of the expected ethyl ester with the melting point 88°-90° C.