trans-4-(t-Butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane → cis 2-(Diethyloxyphosphinoyl)-4-hydroxymethyl-1,3-dithiolane

HRID 618842ノート

反応式

HRID 618842 の反応式
[Si]([O:8][CH2:9][C@@H:10]1[CH2:14][S:13][C@@H:12]([P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])[S:11]1)(C(C)(C)C)(C)C>CO.C(Cl)(=O)C.[Cl-].[NH4+]>[CH2:18]([O:17][P:15]([O:20][CH2:21][CH3:22])([C@H:12]1[S:11][C@@H:10]([CH2:9][OH:8])[CH2:14][S:13]1)=[O:16])[CH3:19]

参加物

5

反応物 1

HCID 131720785trans-4-(t-Butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane

生成物 1

HCID 86752990cis 2-(Diethyloxyphosphinoyl)-4-hydroxymethyl-1,3-dithiolane収率 77.6%

試薬・触媒・溶媒 3

HCID 6367Acetyl chloride触媒HCID 25517Ammonium Chloride触媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of cis-4-(t-butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane (example 49) (3.70 g, 9.56 mmol) in anhydrous methanol (50 mL) was added acetyl chloride (6 drops) at 0° C. The solution was stirred at 0° C. for 30 min and then at room temperature for 4.5 hrs. A saturated solution of ammonium chloride (3 drops) was added and the solution was stirred for 15 min followed by evaporation of solvents. The crude material was purified by flash chromatography with a mixture of dichloromethane and methanol (95:5) to give the compound (2.02 g) in 77% yield.

後処理

  1. waitat room temperature for 4.5 hrs
  2. stirringthe solution was stirred for 15 min
  3. customfollowed by evaporation of solvents
  4. customThe crude material was purified by flash chromatography with a mixture of dichloromethane and methanol (95:5)

出典と根拠

ORDレコード
ord-96d754d797e24fa7b5792f2342e57745
出典データセット
uspto-grants-1999_09
特許番号
US05955610

反応ノート

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