Boron trifluoride etherate → HCID 19373371, compound

HRID 1197328Notes

Reaction equation

HRID 1197328 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-ad2a6af78c0f4e1a8668c901c1fa3a4e
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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