Potassium Carbonate → ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzoate

HRID 384445

反応式

HRID 384445 の反応式
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH:29]=[C:30]([OH:32])[CH:31]=2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]=1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH:29]=[C:30]([O:32][CH2:35][CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH:31]=2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]=1[CH3:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 59527065HCID 59527065、化合物

生成物 1

HCID 59527401ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzoate収率 97.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-hydroxybenzoate (2.10 g), 4-(bromomethyl)tetrahydro-2H-pyrane (2.29 g), potassium carbonate (0.98 g), and DMF (40 mL) was stirred at 80° C. for 13 hours. The reaction mixture was concentrated under reduced pressure, and then water was added to the residue, followed by extraction with ethyl acetate (150 mL). The organic layer was washed sequentially with water and saturated brine, and dried. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzoate (2.50 g).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionwater was added to the residue
  3. extractionfollowed by extraction with ethyl acetate (150 mL)
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

出典と根拠

ORDレコード
ord-2e07592495294ee89e1737827a91f1e2
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

関連ノート

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