Sodium Chloride → 5-(3-Chloropropoxy)-3-(phenylmethoxy)pyridine

HRID 1168948노트

반응식

HRID 1168948 반응식
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:18][CH2:19][CH2:20][CH2:21]I.[Na+].[Cl-]>CN(C)C=O.O>[Cl:18][CH2:19][CH2:20][CH2:21][O:15][C:11]1[CH:10]=[C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:14]=[N:13][CH:12]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 229897043-Benzyloxy-5-hydroxypyridine

생성물 1

HCID 229896985-(3-Chloropropoxy)-3-(phenylmethoxy)pyridine

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

Under a nitrogen atmosphere, a solution of 5-(phenylmethoxy)pyridine-3-ol (1.52 g, 7.56 mmol) in N,N-dimethylformamide (DMF) (10 mL) was added drop-wise over 5 min to a cold (0-5° C.), stirring slurry of sodium hydride (0.238 g of an 80% dispersion in mineral oil, 7.94 mmol) in DMF (15 mL). The mixture was allowed to stir and warm to ambient temperature over 1 h. Next, 1-chloro-3-iodopropane (1.85 g, 9.07 mmol) was added drop-wise over 5 min. The resulting dark-brown mixture was stirred at ambient temperature for 4 h. Water (25 mL) was added, followed by saturated NaCl solution (25 mL), and the mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a residue that was dried briefly under high vacuum to give an oil.

후처리

  1. stirringThe resulting dark-brown mixture was stirred at ambient temperature for 4 h
  2. extractionthe mixture was extracted with ether (4×50 mL)
  3. dry with materialThe combined ether extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation to a residue that
  6. customwas dried briefly under high vacuum
  7. customto give an oil

출처 및 근거

ORD 기록
ord-87e927aeec304c8a91c4153a1559cab3
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627648B1

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