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

HRID 1780066ノート

反応式

HRID 1780066 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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##

後処理

  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)

出典と根拠

ORDレコード
ord-fe68af0547014d299bee20a91055d675
出典データセット
uspto-grants-1997_05
特許番号
US05629428

反応ノート

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