Potassium Carbonate → Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoate

HRID 512925ノート

反応式

HRID 512925 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]4[CH2:22][O:21]4)[CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[SH:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(#N)C>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32][CH2:22][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14](/[CH:13]=[CH:12]/[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[OH:21]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 867207317-Chloro-2-[(E)-2-(3-oxiranyl-phenyl)-vinyl]-quinoline

生成物 1

HCID 86720738Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoate収率 31.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of epoxide 30 (37 g, 0.120 mol) in a mixture of dimethylformamide (140 ml) and acetonitrile (200 ml) was added methyl-2-mercaptobenzoate (20.0 g, 0.145 mol), followed by addition of anhydrous potassium carbonate (19.8 g, 0.145 mol). The reaction mixture was stirred overnight, filtered and concentrated. The resulting mixture was poured into water (2.0 L), stirred and extracted with ethylacetate (1.0 L). The organic layer was washed with water (500 ml) and brine (500 ml), dried over anhydrous sodium sulphate, evaporated and subjected to FC (EtOAc/hexanes) to afford product as a pale yellow solid 46 (18.0 g, 31% yield).

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe resulting mixture was poured into water (2.0 L)
  4. stirringstirred
  5. extractionextracted with ethylacetate (1.0 L)
  6. washThe organic layer was washed with water (500 ml) and brine (500 ml)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated

出典と根拠

ORDレコード
ord-13a21cd34a534b759ff8f3a5b13453a5
出典データセット
uspto-grants-2015_08
特許番号
US09102665B2

反応ノート

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