Dichloromethane → HCID 22342532, compound

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Reaction Steps

To a stirred solution of 2,4-dimethoxythiazole-5-carboxaldehyde (0.01 mol), which may be prepared as described in Step (b) above, in a solvent such as dichloromethane is added phosphorous tribromide or another suitable ether cleaving reagent, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the corresponding 2,4-thiazolidindione-5-carboxaldehyde is formed, the reaction is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over sodium sulfate, and rotary evaporated. The residue is dissolved in THF, and 1 mol equivalent of a suitable non-nucleophilic base as described above in Example 17 is added, followed by 1 mol equivalent of methyl iodide. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the corresponding 2-methoxy-4,5-dihydro-thiazolin-4-one-5-carboxaldehyde is formed, the mixture is partitioned and worked up as described above. The resulting residue is dissolved in THF, and 1 mol equivalent of a suitable non-nucleophilic base as described above in Example 17 is added, followed by 1 mol equivalent of 2,2-difluoro-hex-5-ynoyl chloride, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the desired product is formed, the reaction is partitioned and worked up as described above to give (E)-5-(2,2-difluoro-hex-5-ynoyloxymethylene)-2-methoxy-4,5-dihydro-thiazolin-4-one, which may be purified, if needed or desired, by chromatography on silica gel or crystallization. Also formed is (Z)-5-(2,2-difluoro-hex-5-ynoyloxymethylene)-2-methoxy-4,5-dihydro-thiazolin-4-one, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Provenance & Evidence