Dichloromethane → (E)-Ethyl 4-methyl-5-(prop-1-en-1-yl)isoxazole-3-carboxylate

HRID 1478205노트

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HRID 1478205 반응식
[CH:1](/[B-](F)(F)F)=[CH:2]\[CH3:3].[K+].C(Cl)Cl.Br[C:13]1[O:17][N:16]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:14]=1[CH3:23].C(N(CC)CC)C>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:23][C:14]1[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:16][O:17][C:13]=1/[CH:1]=[CH:2]/[CH3:3]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 49761691Potassium trans-1-propenyltrifluoroborateHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2회

생성물 1

HCID 125490638(E)-Ethyl 4-methyl-5-(prop-1-en-1-yl)isoxazole-3-carboxylate

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

A suspension of potassium trans-1-propenyltrifluoroborate (9.86 g, 66.7 mmol), PdCl2(dppf).DCM adduct (907 mg, 1.11 mmol), ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (13 g) and triethylamine (7.7 mL) in EtOH (250 mL) was degassed under vacuum and back-filled with nitrogen before heating at 90° C. for 18 h. After cooling to room temperature, the reaction was partitioned between EtOAc and brine, separated, dried over MgSO4 and concentrated under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 5-10% EtOAc in iso-hexane afforded the title compound;

후처리

  1. additionback-filled with nitrogen
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was partitioned between EtOAc and brine
  4. customseparated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was adsorbed onto silica and purification by chromatography
  8. washeluting with 5-10% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-c9d8be99ee37425882051e9378c7c96a
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403810B2

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