Dichloromethane methanol → Diethyl (S)-[1-(t-butyldiphenylsilyloxymethyl)-2-hydroxyethoxy]methylphosphonate

HRID 6257

Reaction equation

HRID 6257 reaction equation
C([O:8][CH2:9][C@@H:10]([CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])C1C=CC=CC=1.[H][H].C(Cl)Cl.CO>C(O)C.CO.Cl.[Pd]>[Si:23]([O:22][CH2:21][C@@H:10]([O:11][CH2:12][P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])[CH2:9][OH:8])([C:36]([CH3:38])([CH3:39])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 21226129Dichloromethane methanolHCID 53667746diethyl (S)-[2-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)ethoxy]methylphosphonateHCID 178418361HCID 178418361, compound

Product 1

HCID 54250790Diethyl (S)-[1-(t-butyldiphenylsilyloxymethyl)-2-hydroxyethoxy]methylphosphonateYield 85.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 21893726Hydrochloride methanolCatalystHCID 702EthanolSolvent

Procedure

To a solution of diethyl (S)-[2-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)ethoxy]methylphosphonate (1.90 g, 3.3 mmol) in ethanol (20 ml) containing a trace of methanol/HCl (10 drops), was added 10%Pd-C (1.2 g). The mixture was shaken under an atmosphere of hydrogen at ambient temperature and atmospheric pressure until hydrogen uptake was complete and t.l.c. (SiO2, CH2Cl2 -MeOH, 95:5) indicated no starting material remained. The reaction mixture was filtered, the filtrate evaporated and the residue obtained chromatographed on silica gel (dichloromethanemethanol, 95:5 as eluant) to give the title compound as a colourless oil (1.35 g, 84%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated
  3. customthe residue obtained
  4. customchromatographed on silica gel (dichloromethanemethanol, 95:5 as eluant)

Sources & evidence

ORD record
ord-f1025d795abd4352a2b488c82920f958
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Linked notes

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