Acetyl chloride → 2,2-Dimethyl-6-acetylchroman

HRID 1085030

反応式

HRID 1085030 の反応式
[CH3:1][C:2]1([CH3:12])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O.O>[CH3:1][C:2]1([CH3:12])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13](=[O:15])[CH3:14])[CH:8]=2)[O:3]1

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 1369362,2-Dimethylchroman2 回HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 1820772,2-Dimethyl-6-acetylchroman

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6375Nitromethane溶媒

実験手順

A solution of 5.0 g (30.82 mmol) of 2,2-dimethylchroman (Compound 56) in 50 ml of nitromethane was treated, under nitrogen, with 2.53 g (32.35 mmol) of acetyl chloride followed by 4.4 g (33 mmol) of aluminum chloride. The reaction mixture was stirred at room temperature for 3 hours and then cooled in an ice-bath and treated slowly with 50 ml of 6M HC1. The mixture was diluted with water and extracted with ether. The ether extracts were washed successively with saturated NaHCO3 solution, water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in-vacuo and the resultant residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane) to give the title compound as a white solid. PMR (CDCl3) : & 1.36 (6H, s), 1.84 (2H, t, J~6.8 Hz), 2.54 (3H, s), 2.82 (2H, t, J~6.8 Hz), 6.80 (1H, d, J~8.4 Hz), 7.69-7.76 (2H, m). MS exact mass, m/e 204.1140 (calcd. for C13H16O2, 204.1150).

後処理

  1. temperaturecooled in an ice-bath
  2. additiontreated slowly with 50 ml of 6M HC1
  3. extractionextracted with ether
  4. washThe ether extracts were washed successively with saturated NaHCO3 solution, water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in-vacuo
  7. customthe resultant residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-6351afb3a6604d1fb91e4a65e5f176d7
出典データセット
uspto-grants-1991_04
特許番号
US05006550

関連ノート

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