N-tert-Butyl-N-fluoro-4-methylbenzene-1-sulfonamide → 2-Fluoronaphthalen-1-ol

HRID 1633210노트

반응식

HRID 1633210 반응식
[F:1]N(C(C)(C)C)S(C1C=CC(C)=CC=1)(=O)=O.[C:17]1([O-:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.[K+]>O1CCCC1.CCOCC>[F:1][C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]=1[OH:27]

참가 물질

5

반응물 2

HCID 13222557N-tert-Butyl-N-fluoro-4-methylbenzene-1-sulfonamideHCID 236723231-Naphthalenol, potassium salt (1:1)

생성물 1

HCID 27614032-Fluoronaphthalen-1-ol수율 60%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Potassium hydride (93.6 mg as a 35% oil dispersion, 0.82 mmol) was suspended in anhydrous tetrahydrofuran (2.5 mL) under nitrogen. 1-Naphthol (72 mg, 0.5 mmole) was added and the mixture was stirred until hydrogen evolution ceased (about 5 minutes) to produce potassium naphtholate. N-Fluoro-N-t-butyl-p-toluenesulfonamide (122 mg, 0.5 mmole) was dissolved in anhydrous tetrahydrofuran (2.5 mL) and the solution was added dropwise to the potassium naphtholate. After 20 minutes the reaction mixture was diluted with ether (100 mL), washed with aqueous 1N oxalic acid solution (30 mL), water (30 mL), and saturated aqueous sodium chloride solution (30 mL), and then dried over anhydrous magnesium sulfate. Filtration, removal of solvent under reduced pressure, and purification by flash column chromatography (silica, 25% methylene chloride in hexane) yielded 2-fluoro-1-naphthol (49 mg, 60% yield) as a white crystalline solid. This material, and an additional sample prepared by this procedure, were analyzed and provided the following results: 1H NMR (90 MHz, CDCl3) δ5.58 (b, 1H, OH), 7.00-8.30 (m, 6H, aromatic); 19F NMR (94.1 MHz, CDCl3) -146.78(m); HRMS calcd. for C10H7OF: 162.0480; found: 162.0439.

후처리

  1. washwashed with aqueous 1N oxalic acid solution (30 mL), water (30 mL), and saturated aqueous sodium chloride solution (30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationFiltration, removal of solvent
  4. customunder reduced pressure, and purification by flash column chromatography (silica, 25% methylene chloride in hexane)

출처 및 근거

ORD 기록
ord-4faf783c4ab24594a6bad08d7597a028
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04479901

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