Reaction equation
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][CH3:19])=[O:5].[CH3:21][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[CH3:19][O:18][CH2:17][C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[S:10][C:6]=1[C:4](=[O:5])[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the above-prepared 4-methoxymethyl-2-phenyl-thiazole-5-carboxylic acid methoxy-methyl amide (6.706 g, 22.9 mmole, 1.0 eq) in dry THF (25 ml) at 0° C. was added dropwise a solution of 1.4M methylmagnesium bromide in (3:1) toluene-THF (32.7 ml, 45.8 mmole, 2.0 eq). The resulting tan suspension was stirred under nitrogen at room temperature for 30 minutes, then quenched by the addition of saturated ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a brown oil. Silica gel chromatography using a gradient elution of (9:1) to (4:1) hexanes-ethyl acetate provided the title compound (6.033 g, 81%) as a yellow crystalline solid. 1H NMR (CDCl3): δ 2.7 (s, 3H), 3.5 (s, 3H), 4.9 (s, 2H), 7.4-7.5 (m, 3H), 8.0 (m, 2H).
Workup
- customquenched by the addition of saturated ammonium chloride
- extractionextracted with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto give a brown oil
- washa gradient elution of (9:1) to (4:1) hexanes-ethyl acetate
Sources & evidence
- ORD record
- ord-16340a3d391d429998074ec6474809a9
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06930116B2
Linked notes
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