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

HRID 1445768

反応式

HRID 1445768 の反応式
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

参加物

5

反応物 3

HCID 6342Acetonitrile2 回HCID 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-oxazole2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba4c2a92eedd4af18842cbe06c550aa2
出典データセット
uspto-grants-2010_02
特許番号
US07666871B2

関連ノート

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