Aluminum(III) Chloride → HCID 24880047, compound

HRID 1191986Notes

Reaction equation

HRID 1191986 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:6]([C:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:17]C(C)C)[C:11]=2[O:10][CH:9]=1)=[O:7].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:6]([C:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([OH:17])[C:11]=2[O:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 57421960HCID 57421960, compound

Product 1

HCID 24880047HCID 24880047, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3,4,5-trimethoxybenzoyl)-6-methoxy-7-isopropoxybenzofuran (23 mg, 0.058 mmol, co-distilled with toluene before use) in dry dichloromethane (1 mL) was treated with solid aluminum chloride (16 mg, 0.116 mmol). The reaction mixture was stirred for 20 minutes at room temperature (monitored by tlc) then quenched with saturated ammonium chloride solution and extracted with ethyl acetate (10 mL). The organic layer was washed with water (5 mL), dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by flash chromatography (silica gel, eluent=hexane/diethyl ether/ethyl acetate; 80:19:1) to afford the title compound as a creamy white crystalline solid (18 mg, 86%); 1H NMR (300 MHz, CDCl3) δ 8.04 (s, 1H, C2H), 7.63 (d, 1H, J=8.53 Hz), 7.14 (s, 2H, benzoyl Hs), 7.02 (d, 1H, J=8.38 Hz), 3.97 (s, 3H, OMe), 3.93 (s, 3H, OMe), 3.89 (s, 6H, 2×OMe); 13C NMR (75 MHz, CDCl3) δ 188.73 (CO), 152.82, 151.24, 144.54, 143.30, 141.76, 133.97, 130.87, 120.92, 120.62, 112.43, 109.16, 106.06, 60.62, 56.85, 55.97.

Workup

  1. customthen quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate (10 mL)
  3. washThe organic layer was washed with water (5 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash chromatography (silica gel, eluent=hexane/diethyl ether/ethyl acetate; 80:19:1)

Sources & evidence

ORD record
ord-e6447b1846e2425c854836cad78f5249
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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