Aluminum(III) Chloride → HCID 135899505, compound

HRID 1511255Notes

Reaction equation

HRID 1511255 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:50]=[CH:49][C:10]([CH2:11][N:12]([C:31]2[CH:32]=[N:33][C:34]3[C:39]([CH:40]=2)=[CH:38][CH:37]=[C:36]([O:41]CC2C=CC=CC=2)[CH:35]=3)[C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[CH:15]=2)=[CH:9][CH:8]=1>C1(OC)C=CC=CC=1.CO>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][N:12]([C:31]2[CH:32]=[N:33][C:34]3[C:39]([CH:40]=2)=[CH:38][CH:37]=[C:36]([OH:41])[CH:35]=3)[C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[CH:15]=2)=[CH:49][CH:50]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 25140250HCID 25140250, compound

Product 1

HCID 135899505HCID 135899505, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7519AnisoleSolvent2×

Procedure

A solution of AlCl3 (44 mg, 0.33 mmol) in anhydrous anisole (150 μl) was added to 32 (43 mg, 0.07 mmol) in anhydrous anisole (150 μl) and the resulting solution was stirred at room temperature for 18 hours. The reaction was diluted with MeOH (150 μl) and the solvent was concentrated. The residue was purified via column chromatography (SiO2, 80:20:1 EtOAc:Hexanes:MeOH) to give 33 as a yellow amorphous solid in quantitative yield: 1H NMR (CDCl3, 500 MHz) δ 8.35 (s, 1H), 7.74 (s, 1H), 7.58 (d, J=8.9 Hz, 1H), 7.52 (bs, 1H), 7.37 (m, 1H), 7.31 (m, 1H), 7.25-7.11 (m, 5H), 6.84-6.77 (m, 3H), 6.74 (d, J=8.6 Hz, 1H), 6.67 (d, J=7.6 Hz, 1H), 6.64 (s, 1H), 5.16 (s, 2H), 3.76 (s, 3H), 3.70 (s, 3H), 3.68 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 170.3, 159.4, 159.3, 158.0, 138.8, 135.5, 132.3, 130.4, 130.3, 130.1 (2C), 129.6, 129.1 (2C), 127.1, 123.0, 122.0, 114.9, 114.3 (2C), 113.3, 110.7, 55.8, 55.4, 53.9; IR (film) νmax 2926, 1601, 1506, 1248, 1177, 1030, 818 cm−1; HRMS (ESI+) m/z: [M+H]+ calcd for C32H28N2O5, 521.2076. found, 521.2030.

Workup

  1. concentrationthe solvent was concentrated
  2. customThe residue was purified via column chromatography (SiO2, 80:20:1 EtOAc:Hexanes:MeOH)

Sources & evidence

ORD record
ord-17f8bea1aadb44bb967d9f604faf9841
Source dataset
uspto-grants-2012_07
Patent number
US08212011B2

Reaction notes

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