Boron Trichloride → HCID 10894986, compound

HRID 1109649Notes

Reaction equation

HRID 1109649 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[O:31]C[O:29][C:5]=2[CH:6]=[C:7]([CH2:9][C@@H:10]2[CH2:15][O:14][C:12](=[O:13])/[C:11]/2=[CH:16]/[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH:8]=1.B(Cl)(Cl)Cl>ClCCl>[OH:29][C:5]1[CH:6]=[C:7]([CH2:9][C@@H:10]2[CH2:15][O:14][C:12](=[O:13])/[C:11]/2=[CH:16]/[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[OH:31]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 11144422HCID 11144422, compound

Product 1

HCID 10894986HCID 10894986, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In 10 ml of dichloromethane, 0.84 g (1.96 mmol) of (S)-(E)-3-[1-(5-methoxy-3,4-methylenedioxyphenyl)methyl]-2-(3,4,5-trimethoxybenzylidene)butanolide was dissolved. The solution was added with 4 ml of a 1.0M dichloromethane solution of boron trichloride (4 mmol), followed by stirring at 0° C. for 30 minutes. The solvent was distilled off under reduced pressure. After the residue was dissolved in a mixture consisting of 20 ml of methanol and 6 ml of 2N-HCl, the solution was stirred at 0° C. for 2 hours. The reaction mixture was extracted with ethyl acetate (50 ml×1, 20 ml×2). The organic layers were combined and washed successively with water and saturated NaHCO3, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby 0.79 g of the title compound was obtained as pale yellow oil (yield: 97%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionAfter the residue was dissolved in a mixture
  3. stirringthe solution was stirred at 0° C. for 2 hours
  4. extractionThe reaction mixture was extracted with ethyl acetate (50 ml×1, 20 ml×2)
  5. washwashed successively with water and saturated NaHCO3
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5e45f516e9524fa7a96dbb39b3d74518
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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