Dichloromethane → HCID 22342532, compound

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.

1. customReaction progress

ORD record

ord-2fe01163002349209d5b983e3e418ec2

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06924276B2