Boron trifluoride etherate → HCID 15101165, compound

HRID 1590600Notes

Reaction equation

HRID 1590600 reaction equation
[I:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([O:8][CH2:9][C:10]2([CH:14]3[CH2:17][CH2:16][CH2:15]3)[CH2:13][O:12][CH2:11]2)=[O:7])=[CH:4][CH:3]=1.B(F)(F)F.CCOCC>ClCCl>[CH:14]1([C:10]23[CH2:9][O:8][C:6]([C:5]4[CH:4]=[CH:3][C:2]([I:1])=[CH:19][CH:18]=4)([O:7][CH2:13]2)[O:12][CH2:11]3)[CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 19767479HCID 19767479, compound

Product 1

HCID 15101165HCID 15101165, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-cyclobutyloxetan-3-yl)methyl 4-iodobenzoate (7.42 g, 20 mmol) in dry dichloromethane (80 ml) at -70° C. under nitrogen atmosphere was added boron trifluoride etherate (2 ml). The solution was allowed to warm to room temperature, stirred overnight and then quenched with dry triethylamine (3 ml). The mixture was evaporated to dryness, partitioned between water and dichloromethane and the organic layer was separated, dried over anhydrous potassium carbonate and evaporated. The residue was chromatographed on basic alumina. Elution with hexane: dichloromethane (9:1 v/v) gave 4-cyclobutyl-1-(4-iodophenyl)-2,6,7-trioxabicyclo[2.2.2]octane (2.8 g, 38%) as white crystals.

Workup

  1. customquenched with dry triethylamine (3 ml)
  2. customThe mixture was evaporated to dryness
  3. custompartitioned between water and dichloromethane
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous potassium carbonate
  6. customevaporated
  7. customThe residue was chromatographed on basic alumina
  8. washElution with hexane: dichloromethane (9:1 v/v)

Sources & evidence

ORD record
ord-98673b49bb4e4d3d888061b1afe22099
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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