Boron trifluoride etherate → HCID 19373371, compound

HRID 129277Notes

Reaction equation

HRID 129277 reaction equation
B(F)(F)F.CCOCC.[Br:10][C:11]([Br:30])=[CH:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][C:23]2([CH2:27][CH2:28][CH3:29])[CH2:26][O:25][CH2:24]2)=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl>[Br:30][C:11]([Br:10])=[CH:12][CH:13]1[CH2:14][CH2:15][CH:16]([C:19]23[O:21][CH2:22][C:23]([CH2:27][CH2:28][CH3:29])([CH2:26][O:25]2)[CH2:24][O:20]3)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 193732533-Propyloxetan-3-ylmethyl 4-(2,2-dibromovinyl)cyclohexanecarboxylate

Product 1

HCID 19373371HCID 19373371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride etherate (40 μl) was added to a stirred solution of 3-propyloxetan-3-ylmethyl 4-(2,2-dibromovinyl)cyclohexanecarboxylate (0.57 g) in dry dichloromethane (10 ml) at -70° C. The mixture was allowed to warm to room temperature over 16 hours. Triethylamine (0.6 ml) was then added. The organic phase was washed with 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 3:7 dichloromethane:hexane saturated with ammonia. 1-[4-(2,2-Dibromovinyl)cyclohexyl]-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane was obtained as a colourless oil (0.34 g).

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialbefore drying over anhydrous magnesium sulphate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane

Sources & evidence

ORD record
ord-a9f4a2e589fb4163aa85ce40bd11b8d8
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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