Diethyl Ether → 2-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acid

HRID 579440Notes

Reaction equation

HRID 579440 reaction equation
C([O:5][C:6]([C:8]1[S:12][C:11]([C:13]2[C:14](=[O:24])[O:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([OH:23])[CH:17]=3)=[N:10][C:9]=1[CH3:25])=[O:7])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OCC)C>ClCCl>[OH:23][C:18]1[CH:17]=[C:16]2[C:21]([CH:22]=[C:13]([C:11]3[S:12][C:8]([C:6]([OH:7])=[O:5])=[C:9]([CH3:25])[N:10]=3)[C:14](=[O:24])[O:15]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 1363877692-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acid tert-butyl ester

Product 1

HCID 1363877702-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(7-hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acid tert-butyl ester (387 mg, 1.08 mmol) and anisole (117 μL, 117 mg, 1.08 mmol) in anhydrous dichloromethane (5 mL) was added trifluoroacetic acid (5 mL) and the obtained solution was stirred at room temperature for 6 h. Diethyl ether (30 mL) was added, the precipitate was collected, washed with diethyl ether and dried in air. In this manner the title compound (285 mg, 0.94 mmol, 87%) was obtained as a light brown solid.

Workup

  1. customthe precipitate was collected
  2. washwashed with diethyl ether
  3. customdried in air

Sources & evidence

ORD record
ord-92a337548f80445897935269cabf3ad4
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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