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Sulfuric Acid → 2-(4-Fluorophenyl)-5-(2-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiophene

HRID 1899086
ノート
印刷プレビュー

反応式

HRID 1899086 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14](OC)=[O:15])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.S(=O)(=O)(O)O>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][CH2:14][OH:15])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:20][CH:19]=2)=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 11795515Methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 233727682-(4-Fluorophenyl)-5-(2-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiophene

試薬・触媒・溶媒 1

HCID 3283
Diethyl Ether
溶媒

反応条件

温度
0 °C

実験手順

A mixture of methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetate (1.8 g) and lithium aluminum hydride (0.63 g) in diethyl ether (30 ml) was stirred at 0° C. for 1 hour. Ethyl acetate and 10% sulfuric acid (50 ml) were added, and the resulting mixture was filtered. The organic layer was separated, washed with water, dried and concentrated under reduced pressure. The residual pale yellow oil (1.6 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (2:1). The obtained oil (1.4 g) was pulverized with hexane to give a yellow powder of 2-(4-fluorophenyl)-5-(2-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiophene.

後処理

  1. filtrationthe resulting mixture was filtered
  2. customThe organic layer was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residual pale yellow oil (1.6 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-44239d0051d34d449c0712c761791bb8
出典データセット
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05571810

反応ノート

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