Cesium carbonate → Methyl 4-fluoro-2-[(2S)-oxiran-2-ylmethoxy]benzoate

HRID 270105ノート

反応式

HRID 270105 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[N+](C1C=C(S(O[CH2:26][C@@H:27]2[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:26][C@@H:27]2[CH2:29][O:28]2)[CH:3]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 2775386Methyl 4-fluorosalicylate

生成物 1

HCID 71655301Methyl 4-fluoro-2-[(2S)-oxiran-2-ylmethoxy]benzoate収率 96.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of methyl 4-fluoro-2-hydroxybenzoate (456.3 mg, 1.76 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (300 mg, 1.76 mmol) and Cs2CO3 (687.4 mg, 2.11 mmol) in DMF (4.5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O, organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was opurified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit) to give the subtitled compound (385 mg).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O, organic layer
  2. dry with materialwas dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a3296f6dec6e49f29eb1e5ed177a23ad
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

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