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

HRID 618833노트

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HRID 618833 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. ##STR52##

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-ec45ba7f4c054934951ad76c62d77cb0
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955610

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