Potassium Carbonate → Methyl 3-(benzyloxy)-5-[4-(methanesulfonyl)phenoxy]benzoate

HRID 20491

反応式

HRID 20491 の反応式
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].F[C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1>CN(C=O)C>[C:20]1([CH2:19][O:18][C:16]2[CH:15]=[C:10]([CH:9]=[C:8]([O:7][C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

生成物 1

HCID 53393370Methyl 3-(benzyloxy)-5-[4-(methanesulfonyl)phenoxy]benzoate収率 73.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

Potassium carbonate (3.21 g, 23.2 mmol) was added to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (3.00 g, 11.6 mmol) in DMF (30 mL) followed by addition of 1-fluoro-4-(methylsulfonyl)benzene (2.02 g, 11.6 mmol) and the reaction was heated at 120° C. for 3 h. The solvent was then removed in vacuo and the residue was taken up in saturated aqueous sodium hydrogencarbonate (50 mL) and ethyl acetate (150 mL). The organic layer was separated, washed with 1M aqueous hydrochloric acid (50 mL) then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:4 to 1:1 ethyl acetate:hexanes, afforded the title compound as a colourless oil (3.50 g, 73%).

後処理

  1. customThe solvent was then removed in vacuo
  2. customThe organic layer was separated
  3. washwashed with 1M aqueous hydrochloric acid (50 mL)
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by column chromatography
  8. washeluting with 1:4 to 1:1 ethyl acetate

出典と根拠

ORDレコード
ord-6af20b50dd1745cd86d2fc92c70fc7a5
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

関連ノート

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