Potassium Iodide → Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoate

HRID 1917817ノート

反応式

HRID 1917817 の反応式
[OH:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C>[CH2:17]([O:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 53396387Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

生成物 1

HCID 22667156Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoate収率 77.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
92.5 °C

実験手順

To solution of methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (13.0 g, 0.0572 mol) in DMF (120 mL) and benzyl chloride (7.23 ml, 0.0629 mol), K2CO3 (8.69 g, 0.0629 mol) and potassium iodide (0.949 g, 0.0057 mol) were added. The reaction mixture was heated at 90-95° C. overnight. The solvent was evaporated under vacuum and the residue was taken in ethyl acetate and washed with water and brine. After drying over MgSO4, the solution was concentrated ad purified on silica gel column to yield methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate (13.99 g, 77% yield). 1HNMR (DMSO-d6): δ 7.66 (1H, s), 7.40 (6H, m), 5.27 (2H, s), 3.83 (3H, s), 3.80 (3H, s). LC-MS (ESI) m/z 318 (M+H)+.

後処理

  1. customThe solvent was evaporated under vacuum
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution was concentrated ad
  5. custompurified on silica gel column

出典と根拠

ORDレコード
ord-1433d64ff88c449d9ec941759dd1a7db
出典データセット
uspto-grants-2013_12
特許番号
US08618289B2

反応ノート

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