Ethanol → 3-Chloro-2-octyloxy-5-(4-octyloxyphenyl)pyridine

HRID 1780066노트

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HRID 1780066 반응식
Br[C:2]1[CH:3]=[C:4]([Cl:17])[C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:6][CH:7]=1.[CH2:18]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Cl:17][C:4]1[C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:6][CH:7]=[C:2]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:28][CH:29]=2)[CH:3]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 190499905-Bromo-3-chloro-2-(octyloxy)pyridine

생성물 1

HCID 190500033-Chloro-2-octyloxy-5-(4-octyloxyphenyl)pyridine수율 64.8%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

3.16 g (9.86 mmol) of 5-bromo-3-chloro-2-octyloxypyridine, 2.47 g (9.86 mmol) of 4-octyloxybenzeneboronic acid, 0.11 g (0.10 mmol) of tetrakis(triphenylphosphine)-palladium(0) and 2.09 g (19.72 mmol) of sodium carbonate are heated at 80° C. for 3 hours in 90 ml of toluene, 60 ml of ethanol and 30 ml of water. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and evaporated, and the product is purified by chromatography (silica gel/hexane:ethyl acetate 9:1), giving 2.85 g of 3-chloro-2-octyloxy-5-(4-octyloxyphenyl)pyridine. ##STR22##

후처리

  1. customThe mixture is subsequently partitioned between aqueous sodium chloride solution and ether
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customthe product is purified by chromatography (silica gel/hexane:ethyl acetate 9:1)

출처 및 근거

ORD 기록
ord-fe68af0547014d299bee20a91055d675
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629428

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