Methyl Acrylate → (E)-3-(2-methyl-benzothiazol-6-yl)-acrylic acid methyl ester

HRID 1469649

Reaction equation

I[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[CH:3]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].C(N(CC)CC)C>C(O[Pd]OC(=O)C)(=O)C>[CH3:17][O:16][C:12](=[O:15])/[CH:13]=[CH:14]/[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-iodo-2-methylbenzo[d]thiazole (275 mg, 1 mmol), methyl acrylate (103 mg, 1.2 mmol), diacetoxypalladium (22 mg, 0.1 mmol) and triethylamine (304 mg, 3 mmol) MeCN (8 mL) is heated in a microwave apparatus at 100° C. for 10 min. The solvent is removed under reduce pressure and the residue is purified by flash chromatography (heptane:EtOAc, 2:1) to give (E)-3-(2-methyl-benzothiazol-6-yl)-acrylic acid methyl ester. MS 234.3 (M+1).

Workup

customThe solvent is removed
customthe residue is purified by flash chromatography (heptane:EtOAc, 2:1)

Sources & evidence

ORD record: ord-c7874f8223fe480ba751f892847c0abd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006249B2

Linked notes

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