tert-Butanol → 13,14-Dihydroxydocosanamide

HRID 2165755

反応式

HRID 2165755 の反応式
[C:1]([NH2:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=C\CCCCCCCC.[C:25]([O-:28])(=O)[CH3:26].C([N+]([CH2:36][CH3:37])(CC)CC)C.[C:38](OO)([CH3:41])([CH3:40])C.S([O-])(O)=[O:45].[Na+].[CH3:49][C:50](O)(C)C>[Os](=O)(=O)(=O)=O.CC(C)=O>[OH:45][CH:13]([CH:25]([OH:28])[CH2:26][CH2:49][CH2:50][CH2:40][CH2:38][CH2:41][CH2:36][CH3:37])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([NH2:24])=[O:23]

参加物

8

反応物 5

HCID 6386tert-ButanolHCID 6410tert-Butyl hydroperoxideHCID 102017Tetraethylammonium acetateHCID 5365371ErucamideHCID 23665763Sodium Bisulfite

生成物 1

HCID 1508582013,14-Dihydroxydocosanamide収率 33%

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒

実験手順

To an acetone (150 ml) solution consisting of erucamide (2 g), tetraethyl ammonium acetate (250 mg) and a 70% aqueous solution (1.3 ml) of t-BuOOH was added a 0.5% t-BuOH solution (0.5 ml) of osmium tetraoxide. The mixture was stirred at room temperature for five days. To the reaction mixture was added a 10% solution of sodium hydrogensulfite (30 ml), and the mixture was stirred for 30 minutes. The reaction mixture was subjected to filtration to collect crystals, then the crystals were washed with acetone, followed by drying to afford colorless crystals [728 mg (yield 33%)], m.p. 153 to 154° C.

後処理

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe reaction mixture was subjected to filtration
  3. customto collect crystals
  4. washthe crystals were washed with acetone
  5. customby drying
  6. customto afford colorless crystals [728 mg (yield 33%)], m.p. 153 to 154° C.

出典と根拠

ORDレコード
ord-41c89cb4b4014742aee95083a823f141
出典データセット
uspto-grants-1990_07
特許番号
US04940730

関連ノート

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