Acetyl chloride → 1-(2,2,4,4-Tetramethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

HRID 6548

반응식

HRID 6548 반응식
[CH3:1][C:2]1([CH3:14])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[C:15](Cl)(=[O:17])[CH3:16].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O>[CH3:1][C:2]1([CH3:14])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=2)[O:3]1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 156611252,2,4,4-Tetramethylchroman2회

생성물 1

HCID 156611361-(2,2,4,4-Tetramethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

시약·촉매·용매 1

HCID 6375Nitromethane용매

실험 절차

To an ice bath cooled solution of 2 g (10.53 mmol) of 2,2,4,4-tetramethylchroman (Compound 84) in 25 ml of nitromethane was added, under nitrogen, 941 mg (11.99 mmol) of acetyl chloride followed by 1.59 g (11.92) mmol) of aluminum chloride. The cooling bath was then removed and the mixture stirred at room temperature for 16 h. The mixture was then cooled again in an ice bath and treated with 25 ml of conc. HCl. The mixture was then filtered and the residue washed with methylene chloride. The filtrate was concentrated in vacuo and the resultant residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a yellow oil. PMR (CDCl3): δ 1.38 (6H, s), 1.39 (6H, s), 1.87 (2H, s), 2.56 (3H, s), 6.83 (1H, d, J~8.7 Hz), 7.71 (1H, dd, J~8.7 Hz, 2.1 Hz), 7.98 (1H, d, J~2.1 Hz). MS exact mass, m/e 232.1468 (calcd. for C13H20O2, 232.1464).

후처리

  1. additionwas added, under nitrogen
  2. customThe cooling bath was then removed
  3. temperatureThe mixture was then cooled again in an ice bath
  4. additiontreated with 25 ml of conc. HCl
  5. filtrationThe mixture was then filtered
  6. washthe residue washed with methylene chloride
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe resultant residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-964ba96c58d94d2ea992b45e7a732b3b
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248777

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