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

HRID 1478205ノート

反応式

HRID 1478205 の反応式
[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]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 49761691Potassium trans-1-propenyltrifluoroborateHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-c9d8be99ee37425882051e9378c7c96a
出典データセット
uspto-grants-2016_08
特許番号
US09403810B2

反応ノート

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