Carbon Tetrachloride → 1-Benzyloxy-3-chloromethyl-7-fluoro-naphthalene

HRID 238597ノート

反応式

HRID 238597 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[CH2:25]([O:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([F:43])[CH:41]=2)[CH:36]=[C:35](CO)[CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.O>[CH2:25]([O:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([F:43])[CH:41]=2)[CH:36]=[C:35]([CH2:20][Cl:24])[CH:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

6

反応物 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59326474(4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol

生成物 1

HCID 593265181-Benzyloxy-3-chloromethyl-7-fluoro-naphthalene収率 87.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of triphenylphosphine (2.8 g, 10.6 mmol) in anhydrous tetrahydrofuran (16 mL) was added carbon tetrachloride (5 mL). After the mixture was stirred at room temperature for 10 minutes, (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (1.5 g, 5.3 mmol) was added as a solid under a nitrogen atmosphere. After being stirred at reflux for 2 hours, the resulting mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL×2). The combined aqueous layers were extracted with ethyl acetate (100 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (elution with 5% ethyl acetate in petroleum ether) to afford 1-benzyloxy-3-chloromethyl-7-fluoro-naphthalene (1.4 g, 87.5%) as a white solid.

後処理

  1. stirringAfter being stirred
  2. temperatureat reflux for 2 hours
  3. temperaturethe resulting mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with water (50 mL×2)
  6. extractionThe combined aqueous layers were extracted with ethyl acetate (100 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (elution with 5% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-97156811c77c4f64a561b2c25cc6303a
出典データセット
uspto-grants-2014_02
特許番号
US08642629B2

反応ノート

読み込み中…