Boron trifluoride etherate → HCID 19767508, compound

HRID 1590605Notes

Reaction equation

HRID 1590605 reaction equation
B(F)(F)F.CCOCC.[I:10][C:11]1[CH:30]=[CH:29][C:14]([C:15]([O:17][CH:18]([C:27]#[N:28])[C:19]2([CH:23]3[CH2:26][CH2:25][CH2:24]3)[CH2:22][O:21][CH2:20]2)=[O:16])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:27]([CH:18]1[C:19]2([CH:23]3[CH2:24][CH2:25][CH2:26]3)[CH2:22][O:21][C:15]([C:14]3[CH:13]=[CH:12][C:11]([I:10])=[CH:30][CH:29]=3)([O:16][CH2:20]2)[O:17]1)#[N:28]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 19767505HCID 19767505, compound

Product 1

HCID 19767508HCID 19767508, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride etherate (1 ml) was added to a stirred solution of 1-cyano-1(3-cyclobutyloxetan-3-yl)methyl 4-iodobenzoate (2.3 g, 5.8 mmol) in dry dichloromethane (30 ml) at -70° C. under a nitrogen atmosphere. The solution was allowed to warm to room temperature and was stirred overnight. Triethylamine (1 ml) was added, the solution was evaporated to dryness to leave a gum which was partitioned between water and dichloromethane. The organic layer was separated, dried over anhydrous potassium carbonate and evaporated. The residue was chromatographed on basic alumina, eluting with hexane:dichloromethane (4:1 v/v) to give 3-cyano-4-cyclobutyl-1(4-iodophenyl)-2,6,7-trioxabicyclo[2.2.2]octane as a white solid (1.05 g, 46%).

Workup

  1. customthe solution was evaporated to dryness
  2. customto leave a gum which
  3. customwas partitioned 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. washeluting with hexane:dichloromethane (4:1 v/v)

Sources & evidence

ORD record
ord-be937825ef6b4effba2e92d1e23fbf74
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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