(E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester → 4-(2-Methyl-benzothiazol-6-yl)-butyric acid methyl ester

HRID 881887Notes

Reaction equation

HRID 881887 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4]/[CH:5]=[CH:6]/[C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([CH3:14])[S:13][C:9]=2[CH:8]=1>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([CH3:14])[S:13][C:9]=2[CH:8]=1

Participants

4

Reactant 1

HCID 67505910(E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester

Product 1

HCID 675057084-(2-Methyl-benzothiazol-6-yl)-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Next, a solution of (E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester in THF (10 mL) is hydrogenated over 10% Pd/C (22 mg, 10% wet) at 1 atm for 48 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 4-(2-methyl-benzothiazol-6-yl)-butyric acid methyl ester. MS 250.4 (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-5a02eb9f38714c3bb73e37f4582536a1
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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