Potassium Sodium Tartrate → 4-(Hydroxymethyl)-2-Isopropylthiazole
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:10]1[S:11][CH:12]=[C:13]([C:15](OCC)=[O:16])[N:14]=1)([CH3:9])[CH3:8].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C1COCC1.CCOCC>[OH:16][CH2:15][C:13]1[N:14]=[C:10]([CH:7]([CH3:9])[CH3:8])[S:11][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
A solution of 10 ml (10 mmol) of lithium aluminum hydride in toluene was diluted in a dry flask under N2 atmosphere with 75 ml of THF. The resulting mixture was cooled to 0° C. and treated dropwise with a solution of 3.96 g (20 mmol) of ethyl 2-isopropyl-4-thiazolecarboxylate in 10 ml of THF. After addition, the solution was stirred at 0° C. for 3 h, diluted with ether, and treated with a small amount of aqueous Rochelle's salt. After stirring, the slurry was filtered, washed with ethyl acetate, and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography using 2% methanol in chloroform to provide 2.18 g (69%) of the desired compound, Rf 0.58 (4% methanol in chloroform). 1H NMR (CDCl3) δ 1.39 (d, J=7 Hz, 6H), 2.94 (br, 1H), 3.31 (heptet, J=7 Hz, 1H), 4.74 (s, 2H), 7.04 (s, 1H). Mass spectrum: (M+H)+=158.
Workup
- additionAfter addition
- stirringAfter stirring
- filtrationthe slurry was filtered
- washwashed with ethyl acetate
- concentrationthe combined filtrates were concentrated in vacuo
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-46e029902f7043d8acc6507d20fa2e9a
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06667404B2
Reaction notes
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