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Tributylstannane → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinone

HRID 2943
ノート
印刷プレビュー

反応式

HRID 2943 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 541262165-{[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene}-3-[2-(acetyloxy)ethyl]-2-thioxo-4-thiazolidinone

生成物 1

HCID 538671995-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinone収率 59.7%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

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 1.25l 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

  1. temperaturethe solution heated
  2. temperatureat reflux temperature for an additional 10 minutes
  3. temperatureAfter cooling
  4. washthe mixture was washed with 1.25l of 1N hydrochloric acid
  5. customa precipitate separated
  6. customThe liquid portion was decanted off
  7. customthe resulting residue was purified by chromatography over silica gel
  8. washeluting with a gradient of 25-50% of ethyl acetate in hexane
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3db3491868884e35b394ce60e7488946
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05731336

反応ノート

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