TRANS 5-(t-BUTYLDIPHENYLSILYLOXYMETHYL)-2-(DIETHYLOXYPHOSPHINOYL)-1,3-OXATHIOLANE → Trans-2-(Diethyloxyphosphinoyl)-5-Hydroxymethyl-1,3-Oxathiolane

HRID 636864노트

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HRID 636864 반응식
[Si]([O:18][CH2:19][C@@H:20]1[O:24][C@@H:23]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[S:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>CO.C(Cl)(=O)C.[Cl-].[NH4+]>[CH2:28]([O:27][P:25]([O:30][CH2:31][CH3:32])([C@H:23]1[S:22][CH2:21][C@H:20]([CH2:19][OH:18])[O:24]1)=[O:26])[CH3:29]

참가 물질

5

반응물 1

HCID 131720781TRANS 5-(t-BUTYLDIPHENYLSILYLOXYMETHYL)-2-(DIETHYLOXYPHOSPHINOYL)-1,3-OXATHIOLANE

생성물 1

HCID 86752984Trans-2-(Diethyloxyphosphinoyl)-5-Hydroxymethyl-1,3-Oxathiolane수율 80%

시약·촉매·용매 3

HCID 6367Acetyl chloride촉매HCID 25517Ammonium Chloride촉매HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of cis and trans-5-t-butyldimethylsilyloxymethyl-2-(diethyloxyphosphinoyl)-1,3-oxathiolane (example 25) (4.00 g, 10.8 mmol) in MeOH (30 mL) was added a few drops of acetyl chloride (200 μL) at 0° C. The mixture was stirred at 0° C. for 1 hr. and at room temperature for 18 hr. A few drops of ammonium chloride was added and the solvent was evaporated under reduced pressure. The crude material was purified by several flash chromatography with a mixture of dichloromethane and methanol (96:4) to give 382 mg of the cis isomer , 1.19 g of the trans isomer and 332 mg of the mixture in a total yield of 80% after the first purification.

후처리

  1. waitand at room temperature for 18 hr
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude material was purified by several flash chromatography with a mixture of dichloromethane and methanol (96:4)

출처 및 근거

ORD 기록
ord-6987f2ce568b4971a0e54f131b9f5ce5
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194576B1

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