tert-Butanol → 13,14-Dihydroxydocosanamide

HRID 2165755

반응식

HRID 2165755 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 1508582013,14-Dihydroxydocosanamide수율 33%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-41c89cb4b4014742aee95083a823f141
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940730

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