Boron Trichloride → HCID 86747915, compound

HRID 1109645Notes

Reaction equation

HRID 1109645 reaction equation
B(Cl)(Cl)Cl.[CH3:5][O:6][C:7]1[C:8]2[O:35]C[O:33][C:9]=2[CH:10]=[C:11]([CH2:13][CH:14]2[CH2:19][O:18][C:16](=[O:17])/[C:15]/2=[CH:20]/[C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)[CH:12]=1>ClCCl>[OH:33][C:9]1[CH:10]=[C:11]([CH2:13][CH:14]2[CH2:19][O:18][C:16](=[O:17])/[C:15]/2=[CH:20]/[C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)[CH:12]=[C:7]([O:6][CH3:5])[C:8]=1[OH:35]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 11004468HCID 11004468, compound

Product 1

HCID 86747915HCID 86747915, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (1.0M, 4.7 ml, 4.7 mmol) of boron trichloride was added at 0° C. to a solution of (RS)-(E)-3-[1-(5-methoxy-3,4-methylenedioxyphenyl)methyl]-2-(3,4,5-trimethoxybenzylidene)butanolide (1.0 g, 2.34 mmol) in dichloromethane (5 ml), followed by stirring at the same temperature for 40 minutes. The solvent was distilled off under reduced pressure. The residue was added with 15 ml of methanol and 4N-HCl, followed by stirring at room temperature for 45 minutes. The reaction mixture was dissolved in 20 ml of ethyl acetate. The resulting mixture was washed with water and then with saturated NaCl. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby 747 mg of the title compound were obtained as yellow foam (yield: 77%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionThe residue was added with 15 ml of methanol and 4N-HCl
  3. stirringby stirring at room temperature for 45 minutes
  4. dissolutionThe reaction mixture was dissolved in 20 ml of ethyl acetate
  5. washThe resulting mixture was washed with water
  6. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d5d8369e45f84556a031cddf7ef461ce
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

Loading…