Boron trifluoride etherate → HCID 19046376, compound

HRID 1781556Notes

Reaction equation

HRID 1781556 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]=1[CH2:25][CH:26]=[C:27]([CH3:32])[C:28](=[O:31])[CH:29]=[CH2:30].B(F)(F)F.CCOCC>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]=1[CH2:25][C:26]1[CH2:30][CH2:29][C:28](=[O:31])[C:27]=1[CH3:32]

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 57008461HCID 57008461, compound

Product 1

HCID 19046376HCID 19046376, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solid product prepared in Example ZC-1C, 6-(1,3-dihydro -6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl) -4-methylhexa-1,4-dien-3-one was dissolved in methylene chloride (15 mL) and treated with boron trifluoride etherate (0.5 mL). After 0.5 hours, the reaction was diluted with ethyl acetate and washed with brine, then dried over magnesium sulfate. Filtration, solvent removal and chromatography (silica gel, hexanes/methylene chloride/ether, 4/4/2) gave the product, 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy -5-isobenzofuranylmethyl)-2-methyl cyclopent -2-en -1-one (0.18 g) as a colorless solid m.p. 65.4°-66.8° C.

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration, solvent removal and chromatography (silica gel, hexanes/methylene chloride/ether, 4/4/2)

Sources & evidence

ORD record
ord-9bfcdef938be481b93d518222f755bb0
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

Loading…