Triethylamine → Ethyl 2-fluoro-3-(methacryloyloxy)pentanoate

HRID 1775999노트

반응식

HRID 1775999 반응식
C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[F:17][CH:18]([CH:24]([OH:27])[CH2:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20].[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1COCC1>[F:17][CH:18]([CH:24]([O:27][C:28](=[O:32])[C:29]([CH3:31])=[CH2:30])[CH2:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 79367479Ethyl 2-fluoro-3-hydroxypentanoate

생성물 1

HCID 86684660Ethyl 2-fluoro-3-(methacryloyloxy)pentanoate수율 71.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Under a nitrogen atmosphere, 50 mL of dehydrated THF, 4.63 g (45.8 mmol) of triethylamine and 466 mg (3.82 mmol) of dimethylaminopyridine were added to 6.27 g (38.2 mmol) of the ethyl 2-fluoro-3-hydroxypentanoate at a room temperature. Thereafter, 4.39 g (42.0 mmol) of methacrylic acid chloride was added dropwise over 10 min, and then the mixture was stirred for 2 hrs. After disappearance of the raw material was confirmed by thin layer chromatography (TLC), an aqueous sodium bicarbonate solution was added to stop the reaction. Thereafter, ethyl acetate was added to the reaction liquid and extraction was carried out three times. The organic layer thus obtained was washed with water and saturated brine each once, and dried by adding anhydrous sodium sulfate. Thereafter, the product obtained by distilling off the solvent under a reduced pressure was purified by column chromatography to give 6.38 g (yield: 60%) of ethyl 2-fluoro-3-(methacryloyloxy)pentanoate represented by the following formula.

후처리

  1. customthe reaction
  2. customThe organic layer thus obtained
  3. washwas washed with water and saturated brine each once, and
  4. customdried
  5. additionby adding anhydrous sodium sulfate
  6. customThereafter, the product obtained
  7. distillationby distilling off the solvent under a reduced pressure
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-921c8cb7ac9b469c98264f9ad56f1c20
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09261780B2

반응 노트

불러오는 중…