Hydrochloric Acid → 2,2,4,4,7-Pentamethyl-6-acetylchroman

HRID 6551

反応式

HRID 6551 の反応式
[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[CH:7][CH:8]=2)[O:3]1.[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C)([O-])=O.CCOCC.O>[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[C:7]([C:16](=[O:18])[CH3:17])[CH:8]=2)[O:3]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 156611242,2,4,4,7-Pentamethyl-chroman2 回

生成物 1

HCID 156611372,2,4,4,7-Pentamethyl-6-acetylchroman

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6375Nitromethane溶媒

実験手順

To an ice-bath cooled solution of 1.96 g (9.6 mmol) of 2,2,4,4,7-pentamethyl-chroman (Compound 89) in 30 ml of nitromethane was added under argon 1.059 g (13.5 mmol) of acetyl chloride followed by 1.9 g (14.3 mmol) of aluminum chloride. The reaction mixture was stirred at room temperature for 14 h and then cooled in an ice-bath and treated with 25 ml of conc. HCl. The mixture was warmed to room temperature and diluted with ether and water. The organic layer was separated and the aqueous layer extracted with ether. The organic extracts were combined and washed successively with water, saturated NaHCO3 solution, water again, and saturated NaCl solution, and then dried (MgSO4). The solvent was removed in vacuo and the residue was purified by flash chromatography (silica; 5% ethyl acetate in hexanes) to give the title compound as a pale yellow oil. PMR (CDCl3): 1.36 (6H, s), 1.37 (6H, s), 1.86 (2H, s), 2.49 (3H, s), 2.56 (3H, s), 6.65 (1H, s), 7.74 (1H, s).

後処理

  1. temperaturecooled in an ice-bath
  2. temperatureThe mixture was warmed to room temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ether
  5. washwashed successively with water, saturated NaHCO3 solution, water again
  6. dry with materialsaturated NaCl solution, and then dried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by flash chromatography (silica; 5% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-c5fd59f9b15f4b71be7ea5f13a3755da
出典データセット
uspto-grants-1993_09
特許番号
US05248777

関連ノート

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