N-Iodosuccinimide → Dibenzyl Methylthiomethyl Phosphate

HRID 264581ノート

反応式

HRID 264581 の反応式
[CH3:1][S:2][CH2:3][O:4]CSC.[P:8]([O-])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].IN1C(=O)CCC1=O>C1COCC1.C(OCC)(=O)C>[P:8]([O:4][CH2:3][S:2][CH3:1])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:9]

参加物

6

反応物 3

HCID 120273N-IodosuccinimideHCID 4193600DibenzylphosphateHCID 21902172(Methylsulfanyl)[(methylsulfanyl)methoxy]methane

生成物 1

HCID 18423735Dibenzyl Methylthiomethyl Phosphate収率 75.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of bis(methylthiomethyl)ether (30 mg, 2.34 mmol) and molecular sieves (300 mg) in THF (100 ml) at room temperature was added dibenzyl phosphate (2.74 g, 9.85 mmol) followed by N-iodosuccinimide (608 mg, 2.71 mmol) and the solution was stirred for 4 h. The reaction mixture was then diluted with ethyl acetate and filtered through a pad of celite. The filtrate was treated with a 1:1 (v:v) solution of saturated aqueous sodium bicarbonate and 5% aqueous sodium thiosulfate. The colorless organic extract was then washed with brine, dried over sodium sulfate and concentrated in vacuo to provide 600 mg (69%) of the title compound:

後処理

  1. filtrationfiltered through a pad of celite
  2. additionThe filtrate was treated with a 1:1 (v:v) solution of saturated aqueous sodium bicarbonate and 5% aqueous sodium thiosulfate
  3. extractionThe colorless organic extract
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-24eeec41aee64ca0810a14ca9e3c6132
出典データセット
uspto-grants-1997_07
特許番号
US05646176

反応ノート

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