Potassium Iodide → 6-(3-Methoxypropoxy)indan-1-one

HRID 922443

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HRID 922443 반응식
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.CC1C=CC(S(OC[CH2:24][CH2:25][CH2:26][O:27][CH3:28])(=O)=O)=CC=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:28][O:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70206596-Hydroxy-1-indanoneHCID 86601716Toluene-4-sulfonic acid 4-methoxy-butyl ester

생성물 1

HCID 683099396-(3-Methoxypropoxy)indan-1-one수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To a solution of 6-hydroxyindan-1-one (1.48 g) in acetonitrile (30 mL) were added 4-methoxybutyl 4-methylbenzenesulfonate (2.93 g), potassium iodide (166 mg) and potassium carbonate (2.07 g), and the mixture was heated to stir at 80° C. for 5 hours. To the reaction mixture was added water under ice-cooling, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=7/3), and then triturated with n-hexane/isopropyl ether (2:1) to give 6-(3-methoxypropoxy)indan-1-one [REx(11-1)] (1.1 g) as a colorless powder.

후처리

  1. temperaturethe mixture was heated
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=7/3)
  8. customtriturated with n-hexane/isopropyl ether (2:1)

출처 및 근거

ORD 기록
ord-c11c7a90bafb412ab0c1ba6aabc79425
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278944B2

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