Phosphorus trichloride → HCID 131720783, compound

HRID 365772Notes

Reaction equation

HRID 365772 reaction equation
[Si:1]([O:18][CH2:19][CH:20]1[CH2:24][O:23][CH:22](OCC)[S:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:30][P:31]([O:35]CC)[O:32][CH2:33][CH3:34])[CH3:29].P(Cl)(Cl)Cl>ClCCl.[Cl-].[Zn+2].[Cl-]>[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:24][O:23][C@@H:22]([P:31]([O:32][CH2:33][CH3:34])([O:30][CH2:28][CH3:29])=[O:35])[S:21]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 24387Phosphorus trichlorideHCID 31215Triethyl phosphiteHCID 21255890HCID 21255890, compound

Product 1

HCID 131720783HCID 131720783, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(t-butyldiphenylsilyloxymethyl)-2-ethoxy-1,3-oxathiolane (12.32 g, 30.6 mmol) and triethylphosphite (3.5 mL, 20.4 mmol, 0.66 eq) in dichloromethane (50 mL) were added phosphorus trichloride (890 μL, 10.2 mmol, 0.33 eq) and zinc chloride (catalytic) at 0° C. The solution was stirred at 0° C. for 1 hr and at room temperature for 3 days. The solvent was evaporated and the crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (60:40) to give the pure compound (8.02 g) in 53% yield with a ratio of 2:1 (trans:cis).

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (60:40)

Sources & evidence

ORD record
ord-9d1365a9c4754135a7bca901cbcea279
Source dataset
uspto-grants-2000_10
Patent number
US06127540

Reaction notes

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