1-(Chloromethoxy)-2-methoxyethane → 10-Hexyl-3,7-dimethoxy-4-(2-methoxyethoxymethoxymethyl)-phenothiazine
Reaction equation
[CH2:1]([N:7]1[C:20]2[CH:19]=[CH:18][C:17]([O:21][CH3:22])=[C:16]([CH:23]=[O:24])[C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([O:25][CH3:26])[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[BH4-].[Li+].C(N1C2C=CC(OC)=C(CO)C=2SC2C1=CC=C(OC)C=2)CCCCC.C([Li])CCC.[CH3:60][O:61][CH2:62][CH2:63][O:64][CH2:65]Cl>O1CCCC1.C(OCC)C.CCCCCC>[CH2:1]([N:7]1[C:20]2[CH:19]=[CH:18][C:17]([O:21][CH3:22])=[C:16]([CH2:23][O:24][CH2:60][O:61][CH2:62][CH2:63][O:64][CH3:65])[C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([O:25][CH3:26])[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2.39 g (6.43 mmol) of 10-hexyl-3,7-dimethoxy-phenothiazine-4-carbaldehyde in 30 ml of tetrahydrofuran was reduced with 7.0 ml of lithium borohydride solution (1M in tetrahydrofuran) analogously to that described in Example 4.1.1.da. The resulting 10-hexyl-3,7-dimethoxyphenothiazine-4-methanol was reacted with 4.0 ml of n-butyllithium solution (1.6M in hexane) and 1.0 g (8.0 mmol) of 2-methoxyethoxymethyl chloride analogously to that described in Example 4.1.1.db. After chromatography on silica gel with diethyl ether/hexane (3:2) 2.33 g (78.5%) of 10-hexyl-3,7-dimethoxy-4-(2-methoxyethoxymethoxymethyl)-phenothiazine were obtained as a light yellowish oil.
Sources & evidence
- ORD record
- ord-ac5d2969d28a447096fd0766caebca5e
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811389
Reaction notes
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