[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
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).
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