Isopropanol → 2-(2-Chloro-4-isopropoxyphenoxy)-1,3-thiazole

HRID 404894ノート

反応式

HRID 404894 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[CH:15](O)([CH3:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1

参加物

6

反応物 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 691693943-Chloro-4-(1,3-thiazol-2-yloxy)phenol

生成物 1

HCID 694369042-(2-Chloro-4-isopropoxyphenoxy)-1,3-thiazole収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of Example 9B (2.3 g, 0.01 mol), isopropanol (1.2 mL, 0.015 mol) and triphenylphosphine (3.93 g, 0.015 mol) in dry tetrahydrofuran was added diethyl azodicarboxylate (2.61 g, 0.015 mol) drop wise and the reaction was stirred at room temperature overnight. The solvent was removed and the residue was purified on silica gel (ethyl acetate/hexane, 5˜35%) to give 2.4 g of product as a light yellow oil (89% yield), 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=5.88 Hz, 6H) 4.42-4.57 (m, 1H) 6.76-6.86 (m, 2H) 6.99 (d, J=2.94 Hz, 1H) 7.19 (d, J=3.68 Hz, 1H) 7.23 (s, 1H), MS (ESI) m/z 269.9 (M+H)+.

後処理

  1. customThe solvent was removed
  2. customthe residue was purified on silica gel (ethyl acetate/hexane, 5˜35%)

出典と根拠

ORDレコード
ord-97f736f9d04f494ca8469431e78d3212
出典データセット
uspto-grants-2014_06
特許番号
US08748627B2

反応ノート

読み込み中…