tert-Butyldimethylsilyl chloride → 2-[1-(5-Tert-butyldimethylsilyloxy-3-(naphth-2-ylmethoxy)phenyl)-1-methoxypropyl]thiazole
Reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[S:9]1[CH:13]=[CH:12][N:11]=[C:10]1[Li].[CH2:15]([Mg]I)[CH3:16].[OH:19][C:20]1[CH:21]=[C:22]([O:31][CH2:32][C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=2)[CH:23]=[C:24]([CH:30]=1)[C:25]([O:27][CH2:28]C)=O>>[Si:1]([O:19][C:20]1[CH:21]=[C:22]([O:31][CH2:32][C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=2)[CH:23]=[C:24]([C:25]([C:10]2[S:9][CH:13]=[CH:12][N:11]=2)([O:27][CH3:28])[CH2:15][CH3:16])[CH:30]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Procedure
Ethyl 5-hydroxy-3-(naphth-2-ylmethoxy)benzoate, obtained from ethyl 3,5-dihydroxybenzoate and 2-bromomethylnaphthalene, was reacted with tert-butyldimethylsilyl chloride using the conditions described in the 1st paragraph of the portion of Example 6 which is concerned with the preparation of starting materials and the product so obtained was reacted in turn with thiazol-2-yl-lithium and ethylmagnesium iodide following the procedures described in the portion of Example 3 which is concerned with the preparation of starting materials. There was thus obtained the required starting material in 49% yield (from ethyl 5-hydroxy-3-(naphth-2-ylmethoxy)benzoate) as an oil. This starting material was methylated using the procedure described in Example 3 to give 2-[1-(5-tert-butyldimethylsilyloxy-3-(naphth-2-ylmethoxy)phenyl)-1-methoxypropyl]thiazole as an oil, in 42% yield.
Workup
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Sources & evidence
- ORD record
- ord-6a5d7272de6b488cbd146cfa24d49cb1
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05196422
Reaction notes
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