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Tetrahydrofuran → 1-[4-Methoxy-3-(4-methoxybutyl)phenyl]ethanone

HRID 922454
ノート
印刷プレビュー

反応式

HRID 922454 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1.[Cl-].[Li+].[F-].[K+].[O:20]1CC[CH2:22][CH2:21]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:21](=[O:20])[CH3:22])=[CH:3][C:4]=1[CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 214586274-Bromo-1-methoxy-2-(4-methoxybutyl)benzene

生成物 1

HCID 867078661-[4-Methoxy-3-(4-methoxybutyl)phenyl]ethanone

試薬・触媒・溶媒 1

HCID 178418397
HCID 178418397、化合物
触媒

反応条件

温度
80 °C

実験手順

To a solution of 4-bromo-1-methoxy-2-(4-methoxybutyl)benzene (523 mg) in tetrahydrofuran (10 mL) were added lithium chloride (326 mg), tetrakis(triphenylphosphine)palladium (0) (381 mg) and tri-n-butyltin-1-ethoxyvinyl 91.11 mL), and the mixture was heated to stir at 80° C. for 20 hours. The reaction solution was cooled to room temperature, and then thereto was added aqueous potassium fluoride solution, and the mixture was stirred for 30 minutes. The mixture was extracted with diethyl ether, and then thereto was added 10% hydrochloric acid, and the mixture was stirred for 1 hour. The organic layer was separated, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1) to give 1-[4-methoxy-3-(4-methoxybutyl)phenyl]ethanone [REx(24-1)] (195 mg) as a yellow oil.

後処理

  1. temperaturewas heated
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringthe mixture was stirred for 30 minutes
  4. extractionThe mixture was extracted with diethyl ether
  5. additionwas added 10% hydrochloric acid
  6. stirringthe mixture was stirred for 1 hour
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1)

出典と根拠

ORDレコード
ord-ec3db68129f646a68435292c7338880d
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278944B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート