Triethylamine → 1-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

HRID 444943ノート

反応式

HRID 444943 の反応式
[F:1][C:2]([F:7])([F:6])[C:3](=O)[CH3:4].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(OCC)C.CCCCCC.Cl[Ti](Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:15]=[C:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[CH:12][CH:11]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 9871Methyl trifluoromethyl ketoneHCID 754524-Methoxybenzylamine

生成物 1

HCID 866576701-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

To a stirring solution of trifluoroacetone (7.75 g, 69.2 mmol) in diethyl ether (60 ml) at −40° C. was added 4-methoxybenzyl amine (9.49 g, 69.2 mmol) and triethylamine (14 g, 138 mmol) in diethyl ether (40 ml). A cooled (0° C.) mixture of TiCl4 (6.56 g, 34.6 mmol) in hexane (40 ml) at was added dropwise over 10 minutes and the resulting mixture was allowed to warm up to ambient temperature over 20 mins and stirred at 50° C. for 2.5 h. The inorganic precipitate was removed by filtration and washed with diethyl ether. The filtrate was concentrated in vacuo to afford a yellow oil. Purification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane afforded the title product.

後処理

  1. temperatureA cooled
  2. additionat was added dropwise over 10 minutes
  3. customThe inorganic precipitate was removed by filtration
  4. washwashed with diethyl ether
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a yellow oil
  7. customPurification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-c5f5c3f1a23e459cba49f4438520141d
出典データセット
uspto-grants-2013_07
特許番号
US08476269B2

反応ノート

読み込み中…