Water → HCID 13106154, compound

HRID 2080118Notes

Reaction equation

HRID 2080118 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:11]([C:9]1[S:10][C:6]([CH2:4][OH:3])=[CH:7][N:8]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13106142Ethyl 2-phenoxy-5-thiazolecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13106154HCID 13106154, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Phenoxy-thiazole-5-carboxylic acid ethyl ester described in Preparation Example 114 (384 mg, 1.54 mmol) was dissolved in tetrahydrofuran (5 mL), and lithium aluminum hydride (292 mg, 7.70 mmol) was added at 0° C. The solution was stirred at room temperature for 1 hour, then, at 0° C., water (292 μl), an aqueous solution of 5N sodium hydroxide (292 μl) and water (876 μl) were sequentially added thereto. The reaction solution was filtered through Celite pad, then, the filtrate was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4), and the title compound (270 mg, 1.30 mmol, 85%) was obtained as a white solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite pad
  2. customthe filtrate was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-b8fc7be406c94499a8dcd8ed95170499
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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