Diethyl Ether → HCID 18972543, compound
Reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:14]=3[O:13][C:12]=2[C:24]=1[CH2:25][OH:26].[Cl-].[NH4+].[CH2:29]([O:31][CH2:32][CH3:33])C.[O:34]1CCC[CH2:35]1>>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:14]=3[O:13][C:12]=2[C:24]=1[CH2:25][O:26][CH2:35][O:34][CH2:33][CH2:32][O:31][CH3:29]Participants
Procedure
8.6 ml of n-butyllithium solution (1.6M in hexane) were added dropwise at -78° to a solution of 3.3 g (11.49 mmol) of 3,7-dimethoxy-10-methyl-10H-dibenzo[b,e][1,4]oxazine-4-methanol in 33 ml of absolute tetrahydrofuran, whereby a white precipitate formed. The reaction mixture was brought to 0°, stirred for 30 minutes, treated at 0° with 1.96 ml (1.5 eq.) of 2-(methoxyethoxy)methyl chloride, stirred at room temperature for 1 hour and then poured into ice, saturated ammonium chloride solution and diethyl ether. The organic phase was dried over magnesium sulphate and evaporated. The residue was chromatographed on silica gel with a mixture of ethyl acetate/hexane (1:2), whereupon, after drying in a high vacuum, 4.13 g (95.75%) of 3,7-dimethoxy-4-[[(2-methoxyethoxy)methoxy]methyl]-10-methyl-10H-dibenzo[b,e][1,4]oxazine were obtained as a colourless oil. MS: 375 (M+, 100), 360(11), 270(14), 256(21), 226(14).
Workup
- customformed
- customwas brought to 0°
- stirringstirred at room temperature for 1 hour
- dry with materialThe organic phase was dried over magnesium sulphate
- customevaporated
- customThe residue was chromatographed on silica gel with a mixture of ethyl acetate/hexane (1:2), whereupon
- customafter drying in a high vacuum
Sources & evidence
- ORD record
- ord-690bf560023d49828c486785f116cede
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811389
Reaction notes
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