Water → 5-(Benzyloxy)-2-fluoropyridine

HRID 1812182노트

반응식

HRID 1812182 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 27631086-Fluoropyridin-3-ol

생성물 1

HCID 665998445-(Benzyloxy)-2-fluoropyridine수율 73.5%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-fluoro-5-hydroxypyridine (Combi-block) (1.00 g, 8.84 mmol) in DMF (12 mL) was treated with sodium hydride, 60% dispersion in mineral oil (Alfa-Aesar) (0.88 g, 22.1 mmol) at rt under N2. After stirring for 40 min, benzyl chloride (Aldrich) (3.05 mL, 26.5 mmol) and tetrabutylammonium iodide (Aldrich) (0.33 g, 0.88 mmol) were added, and the reaction mixture was stirred for a further 2 h. Water (2 mL) was added to quench the reaction, and the reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic extracts were washed with sat. NaHCO3, brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (120 g, 10% to 20% actone in hexanes) to give the product as a colorless liquid (1.32 g). m/z (ESI, +ve ion) 204.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.91 (br. s., 1H); 7.32-7.51 (m, 6H); 6.86 (dd, J=8.84, 3.29 Hz, 1H); 5.10 (s, 2H).

후처리

  1. stirringthe reaction mixture was stirred for a further 2 h
  2. customto quench
  3. customthe reaction
  4. customthe reaction mixture was partitioned between EtOAc and sat. NaHCO3
  5. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
  6. washThe combined organic extracts were washed with sat. NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (120 g, 10% to 20% actone in hexanes)

출처 및 근거

ORD 기록
ord-7f925629d0ee49ac8fe4ac1a414c4384
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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