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

HRID 1197312Notes

Reaction equation

HRID 1197312 reaction equation
B(F)(F)F.CCOCC.[C:10]([O:17][CH2:18][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])([CH2:18][O:17]1)[CH2:22][O:21]2)[CH2:12][CH2:13][C:14]#[CH:15]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 19373318(3-Propyloxetan-3-yl)methyl hex-5-ynoate

Product 1

HCID 153007461-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride etherate (0.18 ml) was added to a stirred solution of (3-propyloxetan-3-yl)methyl hex-5-ynoate (1.33 g.) in dry dichloromethane (25 ml) at -70° C. The mixture was allowed to warm to room temperature over 16 hours. Triethylamine (0.28 ml) was then added and the solvent was removed in vacuo. The residue was partitioned between diethyl ether and water. The organic phase was separated and further washed with water and brine before drying over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on alumina eluting with 1:6 dichloromethane:hexane saturated with ammonia. 1-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane was obtained as a colourless oil which crystallised on trituration (0.64 g) with hexane.

Workup

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

Sources & evidence

ORD record
ord-06f88c4119804d68be59c8f4e2ee07ab
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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