Iodine → 2-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

HRID 1445758

反応式

HRID 1445758 の反応式
[I:1]I.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16]O)[N:14]=2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16][I:1])[N:14]=2)=[CH:6][CH:5]=1

参加物

8

反応物 4

HCID 807IodineHCID 1049PyridineHCID 11776TriphenylphosphineHCID 108805302-(2-(4-Bromophenyl)-5-methyloxazol-4-YL)ethanol

生成物 1

HCID 589513942-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Add iodine (1.90 g, 7.49 mmol) to a stirred mixture of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (1.503 g, 5.33 mmol), triphenylphosphine (2.101 g, 8.01 mmol), and pyridine (1.4 mL, 17 mmol) in toluene (48 mL) and heat at 100° C. for 45 min. Cool to room temperature, add ethyl acetate and water, and separate the layers. Extract the aqueous layer twice with ethyl acetate, wash the organic layer with 0.1N HCl, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8.4 Hz, 2H), 7.60 (d, J=8.8 Hz, 2H), 3.49 (dd, J=7.2, 7.2 Hz, 2H), 3.11 (dd, J=7.2, 7.2 Hz, 2H), 2.39 (s, 3H).

後処理

  1. temperatureCool to room temperature
  2. customseparate the layers
  3. extractionExtract the aqueous layer twice with ethyl acetate
  4. washwash the organic layer with 0.1N HCl
  5. dry with materialdry over anhydrous magnesium sulfate
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue
  8. washby flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid

出典と根拠

ORDレコード
ord-ceb9f050bd8e44138dbb19c5551d1f16
出典データセット
uspto-grants-2010_02
特許番号
US07666871B2

関連ノート

読み込み中…