p-Toluenesulfonic acid → Trans 5-(t-Butyldiphenylsilyloxymethyl)-2-(Diethyloxyphosphinoylmethyl)-1,3-Oxathiolane

HRID 481729

반응식

HRID 481729 반응식
C(O[CH:4](OCC)[CH2:5][P:6]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])=[O:7])C.[Si:17]([O:34][CH2:35][CH:36]([OH:39])[CH2:37][SH:38])([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Si:17]([O:34][CH2:35][C@@H:36]1[O:39][C@@H:4]([CH2:5][P:6]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])=[O:7])[S:38][CH2:37]1)([C:30]([CH3:33])([CH3:31])[CH3:32])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 82071Diethyl (2,2-diethoxyethyl)phosphonateHCID 516892Sodium BicarbonateHCID 212558771-t-BUTYLDIPHENYLSILYLOXY-3-MERCAPTO-2-PROPANOL

생성물 1

HCID 131720788Trans 5-(t-Butyldiphenylsilyloxymethyl)-2-(Diethyloxyphosphinoylmethyl)-1,3-Oxathiolane수율 87%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of diethylphosphonoacetaldehyde diethylacetal (12.23 g, 48.1 mmol, 1.2 eq.) and t-butyldiphenylsilyloxy-3-mercapto-2-propanol (13.63 g, 38.1 mmol, 1.2 eq.) in toluene (500 mL) was added PTSA (0.73 g, 3.8 mmol, 0.1 eq.). The mixture was stirred at reflux for 72 hr and was cooled to room temperature. A saturated solution of sodium bicarbonate was added and the aqueous phase was extracted with dichloromethane. The organic phase was dried with anhydrous magnesium sulphate and evaporated under reduced pressure. The crude material was purified by flash chromatography with ethyl acetate:hexane (2:1), and gave 16.31 g of the compound in a 87% yield.

후처리

  1. temperatureat reflux for 72 hr
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe organic phase was dried with anhydrous magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe crude material was purified by flash chromatography with ethyl acetate:hexane (2:1)

출처 및 근거

ORD 기록
ord-e14575929f004883b53f134331baef30
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789394

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