Acetonitrile → 2-(4-Bromo-phenyl)-5-methyl-4-vinyl-oxazole

HRID 1445768

반응식

HRID 1445768 반응식
CN1CCN2CCN(C)P1N(C)CC2.C(#N)C.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]([CH3:33])=[C:28]([CH2:30][CH2:31]I)[N:29]=2)=[CH:21][CH:20]=1>C1COCC1>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:26][C:27]([CH3:33])=[C:28]([CH:30]=[CH2:31])[N:29]=2)=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 6342Acetonitrile2회HCID 41867232,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 589513942-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole2회

생성물 1

HCID 222611552-(4-Bromo-phenyl)-5-methyl-4-vinyl-oxazole수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (3.17 g, 14.7 mmol) as a solution using acetonitrile (10 mL) to a solution of 2-(4-bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole (See Intermediate 30) (4.38 g, 11.1 mmol) in 2.8:1 acetonitrile:THF (190 mL). After 4 hrs, concentrate under reduced pressure and add EtOAc and water to the residue. Separate the layers and extract the aqueous material with EtOAc. Wash the crude organic extract with water, dry over MgSO4, filter and concentrate. Purify on silica gel eluting with 7% EtOAc to give 2-(4-bromo-phenyl)-5-methyl-4-vinyl-oxazole (2.31 g, 83%): 1H NMR (400 Hz): (CDCl3) δ 7.89 (d, 2H, J=8 Hz), 7.57 (d, 2H, J=8 Hz), 6.54 (dd, 1H, J=17, 11 Hz), 5.93 (dd, 1H, J=17, 2 Hz), 5.29 (dd, 1H, J=11, 2 Hz), 2.40 (s, 3H).

후처리

  1. concentrationconcentrate under reduced pressure
  2. additionadd EtOAc and water to the residue
  3. customSeparate the layers
  4. extractionextract the aqueous material with EtOAc
  5. washWash the crude
  6. extractionorganic extract with water
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify on silica gel eluting with 7% EtOAc

출처 및 근거

ORD 기록
ord-ba4c2a92eedd4af18842cbe06c550aa2
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666871B2

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