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

HRID 238597노트

반응식

HRID 238597 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 593265181-Benzyloxy-3-chloromethyl-7-fluoro-naphthalene수율 87.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-97156811c77c4f64a561b2c25cc6303a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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