Triphenylphosphine → 3-{6-Hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoic Acid

HRID 264786

反応式

HRID 264786 の反応式
Br[C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:6][CH:5]=[C:4]([CH2:25][OH:26])[N:3]=1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:51]([O-:55])(=[O:54])[CH:52]=[CH2:53].[K+]>CN(C=O)C.O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Pd](Cl)Cl>[OH:26][CH2:25][C:4]1[N:3]=[C:2]([CH:53]=[CH:52][C:51]([OH:55])=[O:54])[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

参加物

9

反応物 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 4429391Potassium acrylate2 回HCID 196927112-Bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine

生成物 1

HCID 540218973-{6-Hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoic Acid

試薬・触媒・溶媒 4

HCID 24290Palladium Chloride触媒HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine (5.00 g, 11.8 mmol) in DMF (22.8 ml) and water (1.2 ml) were added potassium acetate (2.91 g, 29.7 mmol), tetra-n-butylammonium iodide (4.37 g, 11.8 mmol), triphenylphosphine (0,245 g, 0.94 mmol), palladium chloride (83 mg, 0.47 mmol) and potassium acrylate (3.91 g, 35.4 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 3.3 h. Some potassium acrylate remained undissolved. The mixture was cooled, solids filtered and washed with ethyl acetate (2×60 ml). The filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml). The organic layer was dried and evaporated. The pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%). mp 112°114° C.

後処理

  1. temperatureThe mixture was cooled
  2. filtrationsolids filtered
  3. washwashed with ethyl acetate (2×60 ml)
  4. washThe filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml)
  5. customThe organic layer was dried
  6. customevaporated
  7. customThe pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%)
  8. custommp 112°114° C.

出典と根拠

ORDレコード
ord-ea78dff7ba164da1b7519d695e39162b
出典データセット
uspto-grants-1997_07
特許番号
US05646286

関連ノート

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