[4-Methyl-2-(phenyloxy)-1,3-thiazol-5-yl]methanol → 4-Methyl-2-(phenyloxy)-1,3-thiazole-5-carbaldehyde

HRID 1173041

Reaction equation

HRID 1173041 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:5][C:6]=1[CH2:7][OH:8]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:1][C:2]1[N:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:5][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 57665456[4-Methyl-2-(phenyloxy)-1,3-thiazol-5-yl]methanol

Product 1

HCID 576654864-Methyl-2-(phenyloxy)-1,3-thiazole-5-carbaldehydeYield 80%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst3×HCID 6212ChloroformSolvent

Procedure

A mixture of [4-methyl-2-(phenyloxy)-1,3-thiazol-5-yl]methanol (X-3a) (0.109 g, 0.492 mmol) and MnO2 (0.22 g, 2.56 mmol) in chloroform (2.5 mL) was stirred at RT for 2 h. More MnO2 was added (0.22 g) and continued to stir overnight. Additional MnO2 was added (0.40 g), and the mixture stirred for 3 days. The mixture was filtered through a pad of Celite, and the Celite was washed with EtOAc. The filtrate was concentrated, and the crude material was purified by chromatography (EtOAc/hexanes) to give the title compound as a colorless oil (0.086 g, 80%). 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 7.46 (t, J=8.0 Hz, 2H), 7.33 (t, J=7.4 Hz, 1H), 7.29-7.27 (m, 2H), 2.60 (s, 3H).

Workup

  1. stirringto stir overnight
  2. stirringthe mixture stirred for 3 days
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washthe Celite was washed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. customthe crude material was purified by chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-9ebb8632ab3742e6a6fc912442aa732c
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Linked notes

Loading…