Hydrochloric Acid → (4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol

HRID 1929562노트

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HRID 1929562 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=1)=O.Cl>O1CCCC1>[CH2:22]([O:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[CH:20]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 593265854-Benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester

생성물 1

HCID 59326474(4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

To a slurry of lithium aluminum hydride (1.4 g, 37.4 mmol) in tetrahydrofuran (30 mL) was added a solution of 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (5.8 g, 18.7 mmol) in tetrahydrofuran (30 mL) at 0° C. under a nitrogen atmosphere. After being heated at 60° C. for 1 hour under a nitrogen atmosphere, the resulting mixture was cooled to 0° C. and treated with 1 N hydrochloric acid to quench the reaction. The mixture was extracted with diethyl ether (50 mL×4). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (4.9 g, 93%) as a white solid.

후처리

  1. temperaturethe resulting mixture was cooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with diethyl ether (50 mL×4)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bd7e89314ec94eca9b99bc890d829fc5
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188090B2

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