Boron trifluoride etherate → HCID 15477419, compound

HRID 357630Notes

Reaction equation

HRID 357630 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5]CC)[O:2][CH2:3][CH3:4].[CH3:11][O:12][CH:13](OC)[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([Cl:22])[CH:15]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:11][O:12][CH:13]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([Cl:22])[CH:15]=1)[P:1]([O:2][CH2:3][CH3:4])(=[O:5])[O:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 31215Triethyl phosphiteHCID 18320526HCID 18320526, compound

Product 1

HCID 15477419HCID 15477419, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyl phosphite (3.2 ml, 19 mmol) was added dropwise to a solution of acetal 7 (4.0 g, 18.5 mmol), boron trifluoride etherate (2.3 ml, 19 mmol) and CH2Cl2 (20 ml) at 0° C. After slowly warming the reaction to room temperature (30 min), the solution was partitioned with dilute NaHCO3, dried over Na2SO4, evaporated and purified on silica gel (40%-100% EtOAc/hexanes) to give 4.6 g (77.5%) of phosphonate 8 as a light yellow oil.

Workup

  1. temperatureAfter slowly warming
  2. customthe reaction to room temperature (30 min)
  3. customthe solution was partitioned with dilute NaHCO3
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified on silica gel (40%-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a8f1fb2762db422b9065edaff6e51e20
Source dataset
uspto-grants-1998_11
Patent number
US05840919

Reaction notes

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