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

HRID 1775999ノート

反応式

HRID 1775999 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-921c8cb7ac9b469c98264f9ad56f1c20
出典データセット
uspto-grants-2016_02
特許番号
US09261780B2

反応ノート

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