Nitrogen → 1-(4-(3-Hydroxypropoxy)-3,5-dimethoxyphenyl)ethanone

HRID 531391

반응식

HRID 531391 반응식
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].N#N.Br[CH2:24][CH2:25][CH2:26][OH:27]>C1OCCOCCOCCOCCOCCOC1.CC(C)=O>[OH:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([C:10](=[O:12])[CH3:11])=[CH:6][C:7]=1[O:8][CH3:9]

참가 물질

7

반응물 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 17198Acetosyringone

생성물 1

HCID 896196821-(4-(3-Hydroxypropoxy)-3,5-dimethoxyphenyl)ethanone수율 42.2%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 180Acetone용매

실험 절차

1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone (3.0 g, 15.3 mmol), 18-crown-6 (0.0606 g, 0.229 mmol) and potassium carbonate (2.74 g, 19.9 mmol) were taken in a two neck round bottom flask equipped with a stir bar. The flask was vacuumed and refilled with N2 three times. Acetone (30 mL) was added through syringe and needle. The mixture was stirred at room temperature for 30 minutes, followed by addition of 1-bromo-3-propanol (1.6 mL, 18.3 mmol). The mixture was refluxed for 24 hours and then filtered. Acetone was removed under vacuum to yield the crude product (3.8 g) which was used in the next step without purification. Purification can be performed by column chromatography (30% ethyl acetate and 70% hexane) to get pure product (1.64 g): 1H NMR (300 MHz, DMSO-d6) δ ppm 1.76 (t, J=6.44 Hz, 2H) 2.55 (s, 3H) 3.54 (d, J=5.27 Hz, 2 H) 3.82 (s, 6 H) 4.01 (q, J=7.03 Hz, 2 H) 7.22 (s, 2 H).

후처리

  1. customequipped with a stir bar
  2. temperatureThe mixture was refluxed for 24 hours
  3. filtrationfiltered
  4. customAcetone was removed under vacuum
  5. customto yield the crude product (3.8 g) which
  6. customwas used in the next step without purification
  7. customPurification

출처 및 근거

ORD 기록
ord-403856439d4043b6bebda4b73f3eafba
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353214B2

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