Triisopropyl phosphite → HCID 21255885, compound

HRID 481731Notes

Reaction equation

HRID 481731 reaction equation
[C:1]([O:9][CH2:10][CH:11]1[S:15][CH2:14][CH:13](OC(OC)=O)[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:21]([O:30]C(C)C)([O:26][CH:27]([CH3:29])[CH3:28])[O:22][CH:23]([CH3:25])[CH3:24].C([O-])(O)=O.[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([O:9][CH2:10][CH:11]1[S:15][CH2:14][CH:13]([P:21]([O:26][CH:27]([CH3:29])[CH3:28])([O:22][CH:23]([CH3:25])[CH3:24])=[O:30])[O:12]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8304Triisopropyl phosphiteHCID 516892Sodium BicarbonateHCID 22607112HCID 22607112, compound

Product 1

HCID 21255885HCID 21255885, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-benzoyloxymethyl-5-(methyloxycarbonyloxy)-1,3-oxathiolane (4.80 g, 16.11 mmol) and triisopropyl phosphite (4.77 ml, 19.33 mmol) in dry dichloromethane (100 ml) at 0° C. was added dropwise titanium tetrachloride (1.77 ml, 16.11 mmol). After 2 n at 0° C., the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was then poured into saturated NaHCO3 (100 ml). The mixture was then filtered and the filtrate was partitioned. The aqueous layer was further extracted with dichloromethane (2×) and the combined extracts were washed with brine (1×), dried and concentrated. Chromatography eluting with 25-50% EtAc in hexanes yielded the title compound as a 1:1 cis trans mixture (4.958 g, 79%).

Workup

  1. customat 0° C.
  2. filtrationThe mixture was then filtered
  3. customthe filtrate was partitioned
  4. extractionThe aqueous layer was further extracted with dichloromethane (2×)
  5. washthe combined extracts were washed with brine (1×)
  6. customdried
  7. concentrationconcentrated
  8. washChromatography eluting with 25-50% EtAc in hexanes

Sources & evidence

ORD record
ord-c7eb7d0b4c9e4e4d9eff9ff0458d5587
Source dataset
uspto-grants-1998_08
Patent number
US05789394

Reaction notes

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