Boron trifluoride etherate → HCID 53832065, compound

HRID 370308Notes

Reaction equation

HRID 370308 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]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([O:23][CH3:24])[CH:15]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:11][O:12][CH:13]([C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([O:23][CH3:24])[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 18320530HCID 18320530, compound

Product 1

HCID 53832065HCID 53832065, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyl phosphite (0.98 ml, 5.7 mmol) was added dropwise to a solution of dimethyl acetal 27 (1.08 g, 4.7 mmol), boron trifluoride etherate (1.2 ml, 9.8 mmol) and CH2Cl2 (10 ml) at 0° C. After warming the reaction to room temperature overnight, the solution was partitioned with 3N HCl and the aqueous layer was washed with CH2Cl2 twice. The organic layers were washed with dilute NaHCO3, dried over Na2SO4, decanted and evaporated. The crude residue was purified on a silica gel column, eluting with 0-80% EtOAc/hexanes, to give 1.36 g (86%) phosphonate 28 as a slightly yellow oil.

Workup

  1. temperatureAfter warming
  2. customthe reaction to room temperature overnight
  3. customthe solution was partitioned with 3N HCl
  4. washthe aqueous layer was washed with CH2Cl2 twice
  5. washThe organic layers were washed with dilute NaHCO3
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. customevaporated
  9. customThe crude residue was purified on a silica gel column
  10. washeluting with 0-80% EtOAc/hexanes

Sources & evidence

ORD record
ord-a8ef6daae0e44116863ba8e03e95871a
Source dataset
uspto-grants-2000_10
Patent number
US06140495

Reaction notes

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