Methyl iodide → (R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

HRID 1643264ノート

反応式

HRID 1643264 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([OH:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:17].[CH3:18]I>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([O:16][CH3:18])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:17]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 42077386(R)-4-(4-Fluoro-3-methyl-phenyl)-4-hydroxy-butanoic acid

生成物 1

HCID 59568829(R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the suspension of NaH (373 mg of a 60% dispersion in mineral oil, 9.3 mmol) in 20 mL THF was slowly added (R)-4-(4-Fluoro-3-methyl-phenyl)-4-hydroxy-butanoic acid as a solution in 10 mL THF at 25° C. Methyl iodide (974 mg, 6.9 mmol, 427 μL) was then added dropwise to the mixture. The resulting mixture was stirred for 3 h at room temperature and then the reaction was quenched by the addition of 20 mL of 1M HCl. The mixture was and extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent left the crude product as an oil which was used in the next step without further purification.

後処理

  1. customat 25° C
  2. customthe reaction was quenched by the addition of 20 mL of 1M HCl
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washthe combined organic layers washed with brine (2×20 mL)
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of solvent
  7. waitleft the crude product as an oil which
  8. customwas used in the next step without further purification

出典と根拠

ORDレコード
ord-aecb9b0a7df74de593857e3ba316a2c8
出典データセット
uspto-grants-2012_02
特許番号
US08119692B2

反応ノート

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