Hydrochloric Acid → 1-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

HRID 6544

反応式

HRID 6544 の反応式
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C)([O-])=O.CCOCC>[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=2)[O:5][CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 3167634,4-Dimethylchroman2 回HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 134781601-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6375Nitromethane溶媒

実験手順

To a stirred solution 7.94 g (48.9425 mmol) of 4,4-dimethylchroman (Compound 76) in 70 ml of nitromethane was added under argon 4.0 g (50.96 mmol) of acetyl chloride followed by 6.8 g (51 mmol) of aluminum chloride. This was stirred at room temperature for 5.5 hours and then cooled in an ice bath and treated slowly with 70 ml of 6N hydrogen chloride. The resultant mixture was stirred at room temperature for 10 minutes and then treated with 100 ml ether and the organic layer separated. The organic layer was washed with water, saturated NaHCO3 and saturated NaCl solutions and dried (MgSO4). Solvent was removed in vacuo and the residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes). This was followed by kugelrohr distillation (95-100 degrees C; 0.15 mm) to give the title compound as a colorless oil. PMR (CDCl3): δ 1.40 (6H), 1.95-2.00 (2H, m), 2.58 (3H), 4.25-4.30 (2H, m), 6.83 (1H, d, J~18.0 Hz), 7.62 (1H, dd, J~8.0 Hz, 1.5 Hz), 8.00 (1H, d, J~1.5 Hz).

後処理

  1. temperaturecooled in an ice bath
  2. customthe organic layer separated
  3. washThe organic layer was washed with water, saturated NaHCO3 and saturated NaCl solutions
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo
  6. customthe residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes)
  7. distillationThis was followed by kugelrohr distillation (95-100 degrees C; 0.15 mm)

出典と根拠

ORDレコード
ord-5f176039deb740b6a1362543c95ff2fb
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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