Carbon Tetrachloride → 1-Benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene

HRID 1468329ノート

反応式

HRID 1468329 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)[C:34]=1[CH3:46])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[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])[C:34]=1[CH3:46])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

5

反応物 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59326595(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol

生成物 1

HCID 593265471-Benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of triphenylphosphine (41.6 g, 159 mmol) in dry THF (190 mL) was added CCl4 (59 mL). The reaction mixture was stirred for 10 minutes and (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (21.5 g, 72.6 mmol) was introduced as a solid at room temperature under nitrogen. The resulting solution was refluxed for 2 hours. The solvent was distilled off under reduced pressure, and the residue was diluted with water. The resulting mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Silica gel column chromatography (100-200 mesh, 5% ethyl acetate in hexanes) provided 1-benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene (18.5 g, 81%) as an off-white solid.

後処理

  1. temperatureThe resulting solution was refluxed for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionThe resulting mixture was extracted twice with ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-58856a1f9c7f4ea1930d41d02a80f97b
出典データセット
uspto-grants-2015_04
特許番号
US09000044B2

反応ノート

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