Boron trifluoride etherate → HCID 15477419, compound

HRID 376946Notes

Reaction equation

HRID 376946 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-d98507a8b2234df982e8a49f51247f9a
Source dataset
uspto-grants-2000_02
Patent number
US06022964

Reaction notes

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