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

HRID 486404

반응식

HRID 486404 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eb9d12dd997142e6a29dbf2c6d24972e
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292736

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