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

HRID 618855Notes

Reaction equation

HRID 618855 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4b1c204cfcef40218970530f089e65a9
Source dataset
uspto-grants-1999_09
Patent number
US05955610

Reaction notes

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