反応式
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=S)[N:19]([CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:18]2=[O:29])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][N:19]([CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:18]2=[O:29])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
Under a nitrogen atmosphere, 82.2 g of 5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene}-3-[2-(acetyloxy)ethyl]-2-thioxo-4-thiazolidinone in 950 ml of toluene was heated to 65° C. Tri-n-butyl tin hydride (219.7 g) and AIBN (4.65 g) were added and the solution heated at reflux temperature for an additional 10 minutes. After cooling, the mixture was washed with 1.25 l of 1N hydrochloric acid followed by 500 ml of a saturated sodium chloride solution. The organic layer was stripped and allowed to stand overnight, during which time a precipitate separated. The liquid portion was decanted off, and the resulting residue was purified by chromatography over silica gel, eluting with a gradient of 25-50% of ethyl acetate in hexane. The appropriate fractions were combined and concentrated in vacuo to provide 45.7 g of the desired titled compound, m.p.=152°-155° C.
後処理
- temperaturethe solution heated
- temperatureat reflux temperature for an additional 10 minutes
- temperatureAfter cooling
- washthe mixture was washed with 1.25 l of 1N hydrochloric acid
- customa precipitate separated
- customThe liquid portion was decanted off
- customthe resulting residue was purified by chromatography over silica gel
- washeluting with a gradient of 25-50% of ethyl acetate in hexane
- concentrationconcentrated in vacuo
出典と根拠
- ORDレコード
- ord-11d61068a7134b4fafe8738ee1a038a5
- 出典データセット
- uspto-grants-1997_11
- 特許番号
- US05691367
関連ノート
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