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

HRID 1469650Notes

Reaction equation

HRID 1469650 reaction equation
[CH3:1][O:2][C:3](=[O:16])/[CH:4]=[CH:5]/[C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[CH:7]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[CH:7]=1

Participants

4

Reactant 1

HCID 67505787(E)-3-(2-methyl-benzothiazol-6-yl)-acrylic acid methyl ester

Product 1

HCID 675056953-(2-Methyl-benzothiazol-6-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Next, a solution of (E)-3-(2-methyl-benzothiazol-6-yl)-acrylic acid methyl ester in ethyl acetate (10 mL) is hydrogenated over 10% Pd/C (22 mg, 10% w) at 1 atm for 18 hours. The catalyst is filtered through Celite and the solvent is removed under reduced pressure. The residue is purified by flash chromatography (heptane:EtOAc, 2:1) to give 3-(2-methyl-benzothiazol-6-yl)-propionic acid methyl ester. MS 236.3 (M+1).

Workup

  1. filtrationThe catalyst is filtered through Celite
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is purified by flash chromatography (heptane:EtOAc, 2:1)

Sources & evidence

ORD record
ord-2dfa9b4c579c40a5943b102f6e6785ca
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

Loading…