Methyl iodide → Methyl 2-isopropyl-alpha-[(Z)-methoxy methylene]-4[(E)-styryl]-5-thiazolacetate

HRID 37611Notes

Reaction equation

[OH:1][CH:2]=[C:3]([C:8]1[S:12][C:11]([CH:13]([CH3:15])[CH3:14])=[N:10][C:9]=1/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4]([O:6][CH3:7])=[O:5].CI.[C:26](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:13]([C:11]1[S:12][C:8](/[C:3](=[CH:2]\[O:1][CH3:26])/[C:4]([O:6][CH3:7])=[O:5])=[C:9]([CH:16]=[CH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:10]=1)([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 20 °C

Procedure

The product of Step G was dissolved in 20 ml of acetone and then 3 ml of methyl iodide and 4 g of potassium carbonate were added. The mixture was stirred for 16 hours at 20° C. After bringing the mixture to dryness, the residue was chromatographed on silica, eluting with a hexane--ethyl acetate mixture (8-2) to obtain 1.3 g of the desired product. Thin layer chromatography; Rf=0.20 [eluant: hexane--ethyl acetate (8-2)].

Workup

customthe residue was chromatographed on silica
washeluting with a hexane

Sources & evidence

ORD record: ord-6fd52f8f709d4582a0de53e2f97abcfc
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420340

Reaction notes

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