Ethyl Acetate → 2-(N,N-Diethylamino)-4-(hydroxymethyl)thiazole

HRID 742152Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([C:12]1[S:13][CH:14]=[C:15]([C:17](OCC)=[O:18])[N:16]=1)[CH2:10][CH3:11])[CH3:8].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1COCC1>[CH2:7]([N:9]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][OH:18])[N:16]=1)[CH2:10][CH3:11])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3.14 ml of lithium aluminum hydride in toluene was diluted in a dry flask under N2 atmosphere with 30 ml of THF. The resulting mixture was cooled to 0° C. and treated dropwise with a solution of 1.43 g (6.28 mmol) of ethyl 2-(N,N-diethylamino)thiazole-4-carboxylate in 5 ml of THF. After addition, the solution was allowed to warm slowly to ambient temperature, stirred for 1 h, recooled to 0° C., and treated with a small amount of aqueous Rochelle's salt followed by ethyl acetate. After stirring, the slurry was filtered, washed with additional ethyl acetate, and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography using methanol in chloroform to provide 0.864 g (73%) of the desired compound, Rf 0.17 (4% methanol in chloroform). Mass spectrum: (M+H)+ =187.

Workup

additionAfter addition
temperatureto warm slowly to ambient temperature
customrecooled to 0° C.
stirringAfter stirring
filtrationthe slurry was filtered
washwashed with additional ethyl acetate
concentrationthe combined filtrates were concentrated in vacuo
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-b0bf052bb43a444f8baf0a33ad9f1e86
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05552558

Reaction notes

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