Boron trifluoride etherate → 1-(Pent-4-yn-1-yl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile

HRID 129269Notes

Reaction equation

HRID 129269 reaction equation
B(F)(F)F.CCOCC.[C:10]([O:17][CH:18]([C:26]#[N:27])[C:19]1([CH2:23][CH2:24][CH3:25])[CH2:22][O:21][CH2:20]1)(=[O:16])[CH2:11][CH2:12][CH2:13][C:14]#[CH:15].C(N(CC)CC)C>ClCCl>[CH2:11]([C:10]12[O:16][CH2:20][C:19]([CH2:23][CH2:24][CH3:25])([CH2:22][O:21]1)[CH:18]([C:26]#[N:27])[O:17]2)[CH2:12][CH2:13][C:14]#[CH:15]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 54001474HCID 54001474, compound

Product 1

HCID 1800351-(Pent-4-yn-1-yl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride etherate (0.25 ml) was added to a solution of 1-cyano-1-(3-propyloxetan-3-yl)methyl hex-5-ynoate (0.5 g) in dry dichloromethane (10 ml) stirred at -70° under a nitrogen atmosphere. The resulting solution was allowed to warm to room temperature overnight. Triethylamine (0.38 ml.) was added and the solvent was removed under vacuum. The residue was partitioned between water and diethyl ether. The organic phase was separated and washed with water and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. The residue was purified by column chromatography on alumina eluting with 1:4 dichloromethane:hexane saturated with ammonia. 1-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile was obtained as an oil (0.25 g). Gas-liquid chromatography (g.l.c): OV-17 at 175° produced one peak.

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residue was partitioned between water and diethyl ether
  3. customThe organic phase was separated
  4. washwashed with water and brine
  5. dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo
  6. customThe residue was purified by column chromatography on alumina eluting with 1:4 dichloromethane

Sources & evidence

ORD record
ord-d7c389bbd17a41fd9af1c5f6505dbd60
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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