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

HRID 922443

反応式

HRID 922443 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 683099396-(3-Methoxypropoxy)indan-1-one収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c11c7a90bafb412ab0c1ba6aabc79425
出典データセット
uspto-grants-2016_03
特許番号
US09278944B2

関連ノート

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