Triethyloxonium tetrafluoroborate → HCID 19918621, compound

HRID 1755806Notes

Reaction equation

HRID 1755806 reaction equation
[CH2:1]([CH:8]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.C([O+](CC)CC)C.[N+](=[CH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N-]>C(Cl)Cl>[CH2:1]([CH:8]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][CH:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:9]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 5097903Tert-butyl 2-diazoacetateHCID 19918600HCID 19918600, compound

Product 1

HCID 19918621HCID 19918621, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of the above ketone (19) (8.18 g) in methylene chloride (18 mL) at -78° C. was added a cold solution of triethyloxonium tetrafluoroborate (28 mL, 1N in CH2Cl2). Immediately afterwards t-butyl diazoacetate (4.1 mL) was added and the reaction stirred for 15 min at -78° C. then allowed to slowly warm up in an ice bath. After the cessation of gas evolution (~15 min), the reaction was quenched by the addition of aqueous saturated NaHCO3 (150 mL) and stirred an additional 15 min. The organic phase was removed and the aqueous phase re-extracted with fresh CH2Cl2. The CH2Cl2 phases were then combined, dried over MgSO4 and evaporated. The product (20) was obtained by silica gel chromatography (5.0×100 cm) eluting with 2.5% ethyl acetate in n-hexane (2.11 g, 17.4%). Another later eluting fraction was obtained which corresponded to the other regioisomer (21) (3.71 g, 30.6%).

Workup

  1. temperatureto slowly warm up in an ice bath
  2. customAfter the cessation of gas evolution (~15 min), the reaction was quenched by the addition of aqueous saturated NaHCO3 (150 mL)
  3. stirringstirred an additional 15 min
  4. customThe organic phase was removed
  5. extractionthe aqueous phase re-extracted with fresh CH2Cl2
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-3df365b6ec234f6e80b9cc4cb8a0f00e
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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