Methyl iodide → (S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoic acid

HRID 1643282노트

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HRID 1643282 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([OH:19])[CH2:11][C@H:12]([CH2:16][CH:17]=[CH2:18])[C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:20].[CH3:21]I>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([O:19][CH3:21])[CH2:11][C@H:12]([CH2:16][CH:17]=[CH2:18])[C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[CH3:20]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59568774(S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-hydroxyethyl)pent-4-enoic acid

생성물 1

HCID 59568837(S)-2-((R)-2-(4-Fluoro-3-methylphenyl)-2-methoxyethyl)pent-4-enoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

To a suspension of 217 mg NaH in 20 mL THF was added (S)-2-((R)-2-(4-fluoro-3-methylphenyl)-2-hydroxyethyl)pent-4-enoic acid in 5 mL THF slowly at room temperature. To this mixture was added methyl iodide (289 μL) dropwise followed by stirring for 3 h at 25° C. The reaction was quenched by the addition of 10 mL 1M HCl and then extracted with ethylacetate (3×30 mL). The combined organic layers were washed with brine (2×20 mL) and dried over sodium sulfate. Evaporation of solvent afforded an oil which was used without further purification in the next reaction.

후처리

  1. customThe reaction was quenched by the addition of 10 mL 1M HCl
  2. extractionextracted with ethylacetate (3×30 mL)
  3. washThe combined organic layers were washed with brine (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvent
  6. customafforded an oil which
  7. customwas used without further purification in the next reaction

출처 및 근거

ORD 기록
ord-9d82caf123ad422a898567ab32e2940e
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119692B2

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