Aluminum(III) Chloride → HCID 66927220, compound

HRID 1404083Notes

Reaction equation

HRID 1404083 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:29][CH3:30])=[C:16]2[C:20]=1[N:19]([CH3:21])[CH:18]=[C:17]2[C:22](=[O:28])[C:23]([N:25]([CH3:27])[CH3:26])=O>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:29][CH3:30])=[C:16]2[C:20]=1[N:19]([CH3:21])[CH:18]=[C:17]2[CH:22]([OH:28])[CH2:23][N:25]([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 58303976HCID 58303976, compound

Product 1

HCID 66927220HCID 66927220, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of LiAlH4 (419 mg, 11.03 mmol) in anhydrous THF at 0° C. under a nitrogen atmosphere was added AlCl3 (488 mg, 3.67 mmol) and the reaction mixture was stirred for 10 min. To this slurry was then added compound 6-3 (500 mg, 1.47 mmol) and stirring continued for 30 min by which time MS showed no starting material. The reaction was quenched by adding water, extracted by ether, dried, and concentrated. The crude material was purified by column chromatography to give compound 6-4 (480 mg, 90%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ (ppm) 2.42 (s, 6H), 2.58 (dd, 1H, J=12.4, 9.6), 2.71 (dd, 1H, J=12.4, 3.3), 3.89 (s, 3H), 4.08 (s, 3H), 5.28 (dd, 1H, J=9.2, 3.0), 6.33 (d, 1H, J=8.5), 6.97 (s, 1H), 7.20 (d, 1H, J=8.3). APCI [M+1]: 309, 311, 327, 329.

Workup

  1. waitcontinued for 30 min by which time MS
  2. customThe reaction was quenched
  3. additionby adding water
  4. extractionextracted by ether
  5. customdried
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-ea8fa81d4c574df59cd13d12a34643da
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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