Water → tetrahydro-4-(4-iodophenyl)-4-methoxy-2H-pyran

HRID 230291

反応式

HRID 230291 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17]I.O>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:14][CH3:17])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57033480tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol

生成物 1

HCID 57762532tetrahydro-4-(4-iodophenyl)-4-methoxy-2H-pyran

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Under an argon atmosphere, a solution of tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol (2.99 g) in anhydrous DMF (10 ml) was added dropwise to a suspension of sodium hydride (60 wt %) (432 mg) in anhydrous DMF (20 ml) at room temperature, and the resulting mixture was stirred at room temperature for 75 minutes. Methyl iodide (0.92 ml) was added dropwise to the reaction solution and the resulting mixture was stirred at room temperature for 8.5 hours. Water was added thereto and the resulting mixture was extracted twice with ethyl acetate. Organic layers were washed with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=10/1) to obtain tetrahydro-4-(4-iodophenyl)-4-methoxy-2H-pyran (2.87 g). NMR (H1, CDCl3): δ 1.90-2.02 (4H, m), 2.97 (3H, s), 3.80-3.88 (4H, m), 7.14 (1H, d, J=8.5 Hz), 7.70 (1H, d, J=8.5 Hz)

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 8.5 hours
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. washOrganic layers were washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing anhydrous sodium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-ec2052f962eb4e3db4d1c5504c4b8a05
出典データセット
uspto-grants-2009_07
特許番号
US07566724B2

関連ノート

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