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

HRID 1173040

Reaction equation

HRID 1173040 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:5][C:6]=1[C:7](OCC)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[N:3]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:5][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 576654844-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 57665456[4-Methyl-2-(phenyloxy)-1,3-thiazol-5-yl]methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 4-methyl-2-(phenyloxy)-1,3-thiazole-5-carboxylate (X-2a) (0.18 g, 0.687 mmol) in THF (3 mL) at 0° C. was added a solution of 1M LAH in THF (2.10 mL, 2.10 mmol). The mixture was stirred at 0° C. for 2 h. Water was added (1 mL) followed by a solution of 1M NaOH (1 mL) and water (1 mL). 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 (0.12 g, 80%). 1H NMR (400 MHz, CDCl3) δ 7.40 (t, J=8.0 Hz, 2H), 7.25 (m, 3H), 4.66 (s, 2H), 2.26 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe Celite was washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customthe crude material was purified by chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-70444c8a35d0468b8847455f7ea63fb8
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Linked notes

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