Boron trifluoride etherate → HCID 53832065, compound

HRID 1699456Notes

Reaction equation

HRID 1699456 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.ClC1C=CC(O)=CC=1C(OC)=C1C2CC3CC(CC1C3)C2>>[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 4

HCID 8000Boron trifluoride etherateHCID 31215Triethyl phosphiteHCID 18320530HCID 18320530, compoundHCID 18320539HCID 18320539, compound

Product 1

HCID 53832065HCID 53832065, compoundYield 86.8%

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) 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-82e85c4908b44dc7a0fe55f91737ed72
Source dataset
uspto-grants-2002_02
Patent number
US06346615B1

Reaction notes

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