3-(1-Adamantyl)-4-methoxyphenylacetylene → ethyl 2-[3-(1-Adamantyl)-4-methoxyphenylethynyl]-4-thiophenecarboxylate

HRID 482498Notes

Reaction equation

HRID 482498 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]2

Participants

3

Reactant 2

HCID 152893643-(1-Adamantyl)-4-methoxyphenylacetyleneHCID 15293216Ethyl 5-bromothiophene-3-carboxylate

Product 1

HCID 19063042ethyl 2-[3-(1-Adamantyl)-4-methoxyphenylethynyl]-4-thiophenecarboxylate

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

  1. customthere were obtained
  2. 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.

Sources & evidence

ORD record
ord-e504ec1b4ea945ab9f8dcf83a1363224
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Reaction notes

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