1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57706034, compound

HRID 1662323Notes

Reaction equation

HRID 1662323 reaction equation
[Cl-].[Li+].C[C:4](P(OC)(O)=O)([C:6]([O-:8])=[O:7])C.[CH2:14]1CCN2C(=NCCC2)CC1.[F:25][C:26]([F:38])([F:37])[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=O>CC#N>[F:25][C:26]([F:38])([F:37])/[C:27](/[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=[CH:4]\[C:6]([O:8][CH3:14])=[O:7]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 27597342,2,2-trifluoro-1-(3-methoxyphenyl)ethanoneHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 57706034HCID 57706034, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of lithium chloride (0.623 g, 14.7 mmol) in MeCN (20 mL), were added trimethylphosphonoacetate (available from Aldrich) (1.70 mL, 11.8 mmol), DBU (1.76 mL, 11.8 mmol), and 2,2,2-trifluoro-1-(3-methoxyphenyl)ethanone (available from Oakwood Products Inc.) (2.0 g, 9.80 mmol) at room temperature. The pale yellow mixture was heated to reflux and stirred overnight. The mixture was partitioned between water and EtOAc. The layers were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with 1 N HCl and brine, dried over Na2SO4, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 6.1 (2.49 g, 97.7% yield) as a colorless oil.

Workup

  1. temperatureThe pale yellow mixture was heated
  2. temperatureto reflux
  3. customThe mixture was partitioned between water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with additional EtOAc
  6. washThe combined organic layers were washed with 1 N HCl and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-5c3f9f4993e64b80bcf5d11727a5999f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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