Imidazole → 5-(2-Iodo-ethyl)-2-pentyl-benzoxazole

HRID 1170412ノート

反応式

HRID 1170412 の反応式
[CH2:1]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][C:9]=2[N:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I-:42].Cl.[NH4+]>C1COCC1.C(OCC)C>[I:42][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:8]2[O:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[N:10][C:9]=2[CH:11]=1

参加物

8

反応物 5

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 30165Iodide IonHCID 21905121Ammonium hydrochlorideHCID 687698612-(2-Pentyl-benzoxazol-5-yl)-ethanol

生成物 1

HCID 687659935-(2-Iodo-ethyl)-2-pentyl-benzoxazole

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Under an argon atmosphere, a 0° C. solution of 2-(2-pentyl-benzoxazol-5-yl)-ethanol (1.63 g, 6.99 mmol) in dry THF (49 ml) was treated with triphenyl phosphine (2.018 b, 7.693 mmol) and imidazole (1.05 g, 15.38 mmol). After complete dissolution iodide (1.95 g, 7.69 mmol) was added in small portion so that the reaction temperature never exceeded 4° C. After stirring for 3 hours at 0° C. the reaction mixture was distributed between diethyl ether and saturated aqueous ammonium hydrochloride. The organic layer was evaporated in vacuum, suspended in diethyl ether, filtered and the filtrate concentrated in vacuum. Silica gel chromatography (eluent: pentane/diethyl ether 4/1) followed by crystallization from pentane provided the title compound as colorless crystals. mp: 47.7/48.7° C.

後処理

  1. additionwas added in small portion so that the reaction temperature never exceeded 4° C
  2. customThe organic layer was evaporated in vacuum
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuum
  5. customSilica gel chromatography (eluent: pentane/diethyl ether 4/1) followed by crystallization from pentane

出典と根拠

ORDレコード
ord-015391dce58d41cc9149c0213f1e5c14
出典データセット
uspto-grants-2010_11
特許番号
US07825260B2

反応ノート

読み込み中…