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Tributyl(3,3-dimethylbut-1-en-1-yl)stannane → (E)-Ethyl 5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxylate

HRID 1478176
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HRID 1478176 반응식
C([Sn](CCCC)(CCCC)/[CH:6]=[CH:7]/[C:8]([CH3:11])([CH3:10])[CH3:9])CCC.Br[C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]=1[CH3:31]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C:8]([CH3:9])([CH3:10])/[CH:7]=[CH:6]/[C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]=1[CH3:31]
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참가 물질

5

반응물 2

HCID 10948728Tributyl(3,3-dimethylbut-1-en-1-yl)stannaneHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2회

생성물 1

HCID 131736501(E)-Ethyl 5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxylate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane
용매

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온도
100 °C

실험 절차

(E)-Tributyl(3,3-dimethylbut-1-en-1-yl)stannane (1194 mg, 0.8 mmol) and ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (187 mg, 0.8 mmol) were dissolved in dioxane (6 mL) and the mixture was degassed thoroughly, refilling with nitrogen. Pd(Ph3P)4 (92 mg, 0.080 mmol) was added and the mixture was stirred at 100° C. for 16 hours. The crude reaction mixture was adsorbed onto silica and purification by chromatography eluting with 0-10% EtOAc in iso-hexane afforded the title compound;

후처리

  1. customthe mixture was degassed thoroughly
  2. customThe crude reaction mixture
  3. customwas adsorbed onto silica and purification by chromatography
  4. washeluting with 0-10% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-b7830f39f1214ff6b9e9ada99ad7c4ae
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09403810B2

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