1H-Indene, 2-methyl- → 2-methyl-3-(2-ethyl N-morpholinyl)indene

HRID 486404

反応式

HRID 486404 の反応式
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].C1C2C(=CC=CC=2)C=C1.CCOCC.ClCC[N:33]1CC[O:36][CH2:35][CH2:34]1.[Cl-].[NH4+]>CCOCC.CCCCCC>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([C:3]=1[N:33]1[CH2:34][CH2:35][O:36][CH:12]([CH2:13][CH3:14])[CH2:11]1)=[CH:5][CH:6]=[CH:7][CH:8]=2

参加物

8

反応物 5

HCID 165871H-Indene, 2-methyl-HCID 25517Ammonium ChlorideHCID 767274-(2-Chloroethyl)morpholineHCID 86747629Indene etherHCID 178418339Butyllithium

生成物 1

HCID 190955172-methyl-3-(2-ethyl N-morpholinyl)indene収率 54%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

16.4 g (0.126 mol) 2-methylindene was taken up in 150 ml dry ether under nitrogen atmosphere. A solution of 9.6 g (0.15 mol) n-butyl lithium (2.1 M) in hexane (62 ml) was added dropwise to the indene/ether solution. The resulting solution was stirred at room temperature for 2 hours and a solution of 3.5 g (0.18 mol) N-(2-chloroethyl)morpholine in 100 ml ether was added and stirred overnight. Saturated solution of ammonium chloride was added to the reaction mixture and the ether layer was extracted with 2N HCl. The acidic aqueous layer was then washed with ether twice and cooled in an ice bath, then neutralized with 35% sodium hydroxide and extracted with ether to give 16.3 g (54%) of the 2-methyl-3-(2-ethyl N-morpholinyl)indene (Formula II Rz=methyl; R3=R4=hydrogen; Alk=1,2-ethylene).

後処理

  1. stirringstirred overnight
  2. extractionthe ether layer was extracted with 2N HCl
  3. washThe acidic aqueous layer was then washed with ether twice
  4. temperaturecooled in an ice bath
  5. extractionextracted with ether

出典と根拠

ORDレコード
ord-eb9d12dd997142e6a29dbf2c6d24972e
出典データセット
uspto-grants-1994_03
特許番号
US05292736

関連ノート

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