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

HRID 636873노트

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HRID 636873 반응식
[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]

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 6367Acetyl chloride촉매HCID 25517Ammonium Chloride촉매HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fb49b28cf0d44aef955dd05f3ca728ca
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194576B1

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