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Sodium Sulfate → N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl)acetamide

HRID 1451588
ノート
印刷プレビュー

反応式

HRID 1451588 の反応式
[C:1]([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=1)([C:11](OCC)=[O:12])[C:6](OCC)=[O:7])(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=1)([CH2:6][OH:7])[CH2:11][OH:12])(=[O:3])[CH3:2]
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 24436Sodium SulfateHCID 98457531,3-Diethyl 2-(acetylamino)-2-(2-(4-octylphenyl)ethyl)propanedioateHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 10521783N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl)acetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution (100 ml) of diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate (11.55 g) in anhydrous tetrahydrofuran was dropwise added to a solution (260 ml) of lithium aluminum hydride (3.0 g) in anhydrous tetrahydrofuran under ice-cooling. The mixture was stirred for 1 hour under ice-cooling and then at room temperature for 2 hours. A saturated aqueous solution of sodium sulfate was dropwise added under ice-cooling to decompose lithium aluminum hydride, which was then filtered off. The resultant mixture was extracted with ethyl acetate and the ethyl acetate layer was washed and dried. The solvent was distilled away and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give crystals of 2-acetamido-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol, melting point 66°-68° C. The obtained compound was dissolved in pyridine (40 ml) and acetic anhydride (30 ml) was added thereto under ice-cooling. The mixture was left standing at room temperature overnight. The reaction mixture was poured into a 10% aqueous hydrochloric acid solution (500 ml) and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous potassium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1) to give 8.25 g of the subject compound.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. waitat room temperature for 2 hours
  4. temperaturecooling
  5. filtrationwas then filtered off
  6. extractionThe resultant mixture was extracted with ethyl acetate
  7. washthe ethyl acetate layer was washed
  8. customdried
  9. distillationThe solvent was distilled away
  10. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

出典と根拠

ORDレコード
ord-67ee0fabf993451183d3b08aa7b543df
出典データセット
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05604229

反応ノート

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